An aromatic amination approach towards ancistrocladinium A/B

Synlett

Volumn , Issue 6, 2010, Pages 939-943

  Buckley, Benjamin R ^a   Christie, Steven D R ^a   Elsegood, Mark R J ^a   Gillings, Claire M ^a   Page, Philip C Bulman ^b   Pardoe, William J M ^a  

^a LOUGHBOROUGH UNIVERSITY   (United Kingdom)

^b UNIVERSITY OF EAST ANGLIA   (United Kingdom)

Author keywords

Amination; Buchwald Hartwig; Natural products; Palladium; Tetrahydroisoquinoline; Tetrahydroquinoline

Indexed keywords

ALKALOID DERIVATIVE; ANCISTROCLADINIUM A; ANCISTROCLADINIUM B; CARBON; ISOQUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AMINATION; ARTICLE; BUCHWALD HARTWIG AMINATION; CHEMICAL BOND; CHEMICAL STRUCTURE; DIONCOPHYLLACEAE; DRUG SYNTHESIS; METHODOLOGY; NONHUMAN; POLYMERIZATION; RING OPENING;

EID: 77949884445     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219561     Document Type: Article

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15. General Procedure A 50 mL round-bottomed flask was charged with Pd2(dba)3 (0.088 mmol), (±)-BINAP (0.18 mmol), and toluene (6 mL). The resulting solution was degassed for 10 min before being heated to 110 C for 15 min. The reaction mixture was allowed to cool to r.t. before NaOt-Bu (4.1 mmol), the aryl bromide (2.2 mmol), and tetrahydroquinoline or tetrahydroisoquinoline (4.4 mmol) were added. The resulting mixture was heated under reflux for 416 h, before being cooled to r.t. and filtered through a pad of Celite®. Solvents were removed under reduced pressure and the crude material purified by column chromatography (silica gel, 99:1 light PEEtOAc). Data for Compound 9 Colorless solid, 99% yield (0.56 g). IR (thin film): nmax = 1627, 1265, 740 cm1. 1H NMR (400 MHz, CDCl3): d = 3.04 (2 H, t, J = 11.6 Hz, CH2CH2), 3.67 (2 H, t, J = 11.6 Hz, CH2CH2), 4.51 (2 H, s, CH2), 7.177.21 (5 H, m, ArH), 7.267.28 (1 H, m, ArH), 7.337.36 (1 H, m, ArH), 7.39 7.41 (1 H, m, ArH), 7.767.68 (3 H, m, ArH). 13C NMR (100 MHz, CDCl3): d = 29.19 (CH2), 47.18 (CH2), 51.13 (CH2), 109.37 (ArCH), 118.73 (ArCH), 123.01 (ArCH), 126.10 (ArCH), 126.29 (ArCH), 126.42 (ArCH), 126.58 (ArCH), 126.60 (2 ArCH), 127.46 (ArCH), 128.07 (ArC), 128.64 (ArCH), 128.84 (ArCH), 134.36 (ArC), 134.76 (ArC), 148.39 (ArCN). MS (FAB+): m/z (%) = 259 (100) [M+], 258 (64). HRMS (ES): m/z calcd for [C19H17N]: 259.1361; found [M+]: 259.1365.
16. We have found that isolation of isoquinolinium salts as crystalline solids can be easily achieved when counterion exchange with sodium tetraphenylborate is carried out. See, for example, ref. 7a.
17. Crystal Data for 18 C19H17N, M = 259.34, a = b = 7.0515 (8), c = 28.297 (3) Å, a = b = g = 90, V = 1407.0(3) 3. pale yellow crystal, 1.04 0.47 0.25 mm3, Dcalc = 1.224 g cm3, m = 0.071 mm1; 13580 data, 1247 unique (Rint = 0.0757). Data were measured on a Bruker APEX II diffractometer with MoKa radiation at 150 K.15 Data were corrected for absorption. The structure was solved by direct methods and refined on F2 values.16,17 Half the molecule is unique and the structure is 50/50 disordered at C(2A)/C(2X) and at N(1)/C(10). R = 0.0489 [for 1134 observed data with F2 > 2s(F2)] and wR = 0.1278 (for all data). Crystal data have been deposited with the Cambridge Crystallographic Data Centre. CCDC: 758059. Data can be retrieved in CIF format by quoting the relevant deposition number in an e-mail request to deposit@ccdc.cam.ac.uk.
18. SAINT and APEX 2 (2008) software for CCD diffractometers. Bruker AXS Inc., Madison, USA.
19. Sheldrick G M., SHELXTL User Manual, Version 6.10 Bruker AXS Inc. Madison USA 2000
20. Sheldrick G M., Acta Crystallogr. 2008 A64 112