Selective C-3 lithiation of 2,3-dibromo- and 2,3-diiodo-1-methylindoles

Tetrahedron Letters

Volumn 47, Issue 48, 2006, Pages 8535-8537

  Ueda, Ikuko ^a   Nishiura, Mitsuko ^a   Takahashi, Tohru ^a   Eda, Kazuo ^a   Hashimoto, Masao ^a   Yamamura, Kimiaki ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

2,3 Dibromo 1 methylindole; 2,3 Diiodo 1 methylindole; 2 Bromo 3 lithio 1 methylindole; 2 Iodo 3 lithio 1 methylindole; Selective 3 lithiation of 2,3 dihalo 1 methylindole

Indexed keywords

INDOLE DERIVATIVE; LITHIUM DERIVATIVE; TERT BUTYLLITHIUM; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; LITHIATION; REACTION ANALYSIS; TEMPERATURE SENSITIVITY; X RAY ANALYSIS;

EID: 33750302489     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.09.160     Document Type: Article

References (13)

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10. 2) = 0.0845, for 1276 (I > 2σ(I)) and independent 1432 reflections, respectively. Parameters were 101 and S = 1.070. Max shift/esd = 0.000.
11. Unpublished results from our laboratory.
12. 2) = 0.5519, for 1136 (I > 2σ(I)) and independent 6116 reflections, respectively. Parameters were 419 and S = 1.005. Max shift/esd = 0.001. We could obtain only twinned crystals for this compound. The relatively large R values are due to the twinning.
13. There is a possibility that 3-halo-2-lithio-1-methylindoles, which were formed initially, changed to the corresponding 2-halo-3-lithio-1-methylindoles.