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Synlett

Volumn , Issue 12, 2008, Pages 1845-1851

Double functionalization of N-Boc-3-(tosylmethyr)indole exploiting the activating properties of the tosyl group

(3) Palmieri, Alessandro a Petrini, Marino a Shaikh, Rafik R a

a UNIVERSITY OF CAMERINO (Italy)

Author keywords

Carbanions; Eliminations; Indoles; Nucleophilic additions; Sulfones

Indexed keywords

INDOLE DERIVATIVE; N BUTYLOXYCARBONYLPROLINE 3 (TOSYLMETHYL)INDOLE; SODIUM HYDROXIDE; TOLUENESULFONIC ACID DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; SUBSTITUTION REACTION;

EID: 48349103444 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078510 Document Type: Article

Times cited : (18)

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- Synthesis of N-Boc-3-(Tosylmethyl) indole (11) To a solution of N-Boc-3-(bromomethyl) indole (5 mmol, 1.55 g) in DMF (10 mL, Bu4NI (0.5 mmol, 0.18 g) and ToISO2Na were added at r.t. After stiring for 2 h at this temperature, cold H2O (30 mL) was added and the mixture was extracted with EtOAc (3 x 30 mL, The organic phase was dried over MgSO4, and after removal of the solvent the residue was purified by column chromatography (hexanes-EtOAc, 8:2) giving 1.54 g (80% yield) of pure 11 as a white solid; mp 124-126°C IR (Nujol, 1374, 1151 cm1. 1H NMR (400 MHz, CDCl3, δ, 1.63 (s, 9 H, 2.37 (s, 3 H, 4.42 (s, 2 H, 7.08-7.12 (m, 1 H, 7.19 (d, 2 H, J, 10.7 Hz, 7.21-7.28 (m, 2 H, 7.45 (s, 1 H, 7.59 (d, 2 H, J, 8.5 Hz, 8.09(d, 1 H, J, 8.1, 13C NMR 75 MHz, CDCl 3, δ, 21.7, 28.2, 54.0, 84.3, 107.9, 115.2, 119.0
- 3): δ = 21.7, 28.2, 54.0, 84.3, 107.9, 115.2, 119.0, 122.9, 124.8, 126.2, 127.4, 128.7, 129.7, 135.2, 136.7, 144.9, 149.8.

29
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- Reaction of N-Boc-3-(Tosylmethyl) indole (11) with Electrophiles To a mixture of NaH (2 mmol) in anhyd DMF (5 mL, sulfonyl indole 11(1 mmol) was added at 0°C. After 20 min stirring at this temperature, the electrophile (1.1 mmol) was added and stirring was continued for the appropriate time at 0°C (see Table 1, The mixture was then cautiously quenched by addition of cold H2O and then acidified with AcOH. After extraction with Et2O (3 x 15 mL) the organic phase was dried over MgSO4 and after removal of the solvent the residue was purified by column chromatography (hexanes-EtOAc, 8:2, Spectroscopic Data for Representative Compounds Compound 12a: mp 58-60°C. IR(Nujol, 1598, 1370, 1155 cm-1. 1H NMR (400 MHz, CDCl 3, δ, 1.67 (s, 9 H, 2.35 (s, 3 H, 2.83-3.06 (m, 1 H, 3.10-3.28 (m, 1 H, 4.39 (dd, 1 H, J, 4.0, 11.4 Hz, 4.92-5.12 m, 2 H, 5.52-5.75
- 3): δ = 21.7, 24.1, 28.3, 31.1, 51.8, 62.5, 84.6, 111.9, 115.4, 119.4, 123.0, 125.0, 126.6, 129.3, 129.6, 134.5, 135.4, 144.9, 149.8, 172.8.

30
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- The free NH on the indole ring is mandatory for a successful process since none of the nucleophilic reagents tested in this reaction gives any result with N-Boc indoles 12
- The free NH on the indole ring is mandatory for a successful process since none of the nucleophilic reagents tested in this reaction gives any result with N-Boc indoles 12.

31
- 48349096730
- Deprotection of N-Boc Sulfonyl Indoles 12 and Their Reaction with Nucleophiles N-Boc indole 12 (1 mmol) was dissolved in a mixture of TFA-CH2Cl2 (1:1, 10 mL) and stirring was continued for 3 h at r.t. After evaporation of the solvents at reduced pressure, the crude sulfonyl indole was purified by column chromatography (hexanes-EtOAc, 8:2, Reaction of sulfonyl indoles 13 with nucleophiles was carried out according to our previously published procedure (ref. 10c, Spectroscopic Data for Representative Compounds Compound 14a: oil. IR (neat, 3393, 1739, 1603, 1463 cm-1. 1HNMR (400 MHz, CDCl3, δ, 0.86 (t, 2.3 H, J, 7.3 Hz, 1.27 (t, 2.5 H, J, 6.8 Hz, 1.28 (t, 1.2 H, J, 7.3 Hz, 2.55-2.69 (m, 2 H, 3.84-3.92 (m, 3 H, 4.16-4.28 (m, 3 H, 4.87-4.99 (m, 2 H, 5.61-5.68 (m, 1 H, 7.02 (d, 1 H, J, 2.1 Hz, 7.08-7.18 (m, 2 H, 7.31 d, 1 H
- 3): δ = 21.8, 26.8, 34.9, 45.7, 93.0, 111.5, 113.3, 116.7, 119.7, 120.1, 122.4, 123.4, 128.3, 136.1, 136.2.

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