Ethyl 5-Bromoindole-2-carboxylate → (5-Bromo-1H-indol-2-yl)methanol

HRID 2212156Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11](OCC)=[O:12])=[CH:5]2.[Al].[Li]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH2:11][OH:12])=[CH:5]2

Participants

Reactant 2

HCID 259091Ethyl 5-Bromoindole-2-carboxylate

HCID 16211445Aluminum;lithium

Product 1

HCID 13567955(5-Bromo-1H-indol-2-yl)methanol

Procedure

The title compound was prepared from ethyl 5-bromo-1H-indole-2-Carboxylate and lithium aluminum in substantially the same manner, as described in step 3 of Example 1. The product was obtained as a solid; mp: 111–112° C. Mass spectrum (ESI, [M−H]−) m/z 224. 1H NMR (400 MHz, DMSO-d6) δ 7.62 (s, 1H), 7.27 (d, 1H, J=8.02 Hz), 7.12 (d, 1H, J=8.02 Hz), 6.25 (s, 1H), 5.29 (t, 1H, J=5.50 Hz), 4.59 ppm (d, 2H, J=5.65 Hz).

Workup

customThe product was obtained as a solid

Sources & evidence

ORD record: ord-1c579038718946128de75d9b508f964b
Source dataset: uspto-grants-2006_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07101903B2

Reaction notes

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