5-Bromo-1H-indole-2-carbaldehyde → 5-butyl-1H-indole-2-carbaldehyde

HRID 629160Notes

Reaction equation

HRID 629160 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]=[O:12])=[CH:5]2.[CH2:13]([B-](F)(F)F)[CH2:14][CH2:15][CH3:16].[K+]>>[CH2:13]([C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([CH:11]=[O:12])=[CH:5]2)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 2

HCID 135224625-Bromo-1H-indole-2-carbaldehydeHCID 23693579Potassium butyl(trifluoro)borate(1-)

Product 1

HCID 1182227845-butyl-1H-indole-2-carbaldehydeYield 28%

Procedure

5-Butyl-1H-indole-2-carbaldehyde was synthesized as in Example 3.1 using 5-bromo-1H-indole-2-carbaldehyde (300 mg, 1.34 mmol) in place of 5-bromo-2-formylfuran and potassium butyltrifluoroborate (352 mg, 2.21 mmol) in place of hexylboronic acid to give 5-butyl-1H-indole-2-carbaldehyde (75 mg, 28%). Used without further characterization.

Sources & evidence

ORD record
ord-8969cf2de75e43a9ac7c4bbf7d30c1b7
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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