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

HRID 629162Notes

Reaction equation

HRID 629162 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(O)O)[CH2:14][CH:15]([CH3:17])[CH3:16]>>[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][CH:15]([CH3:17])[CH3:16]

Participants

3

Reactant 2

HCID 135224625-Bromo-1H-indole-2-carbaldehydeHCID 15061386(3-Methylbutyl)boronic acid

Product 1

HCID 1182227305-isopentyl-1H-indole-2-carbaldehydeYield 37.1%

Procedure

5-Isopentyl-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 isopentylboronic acid (256 mg, 2.21 mmol) in place of hexylboronic acid to give 5-isopentyl-1H-indole-2-carbaldehyde (107 mg, 37%). Used without further characterization.

Sources & evidence

ORD record
ord-780cec33bde64040baca470e625b4dc7
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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