Indole → 4,5-dimethyl-1H-indole-3-carboxylic acid

HRID 57316

Reaction equation

[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.CB(O)O.[C:14]([O-:17])([O-])=[O:15].[K+].[K+].O1[CH2:25][CH2:24]OCC1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:6][C:5]1[C:24]([CH3:25])=[CH:7][CH:8]=[C:9]2[C:4]=1[C:3]([C:14]([OH:17])=[O:15])=[CH:2][NH:1]2

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of bromide 1 (1.0 g, 4.78 mmol), methyl boronic acid (860 mg, 14.3 mmol), Pd(dppf)2Cl2 (194 mg, 0.239 mmol), and K2CO3 (1.32 g, 9.56 mmol) in dioxane (20 mL) was degassed and stirred at 90° C. for 5 h under nitrogen. The reaction mixture was concentrated, and the residue was purified by silica gel chromatography (EtOAc/petroleum ether=1/4) to give the desired product (636 mg, 4.39 mmol, 91.8%) as a white solid.

Workup

customwas degassed
concentrationThe reaction mixture was concentrated
customthe residue was purified by silica gel chromatography (EtOAc/petroleum ether=1/4)

Sources & evidence

ORD record: ord-bc86db76d4f148378e7240faa3b5a944
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09434724B2

Linked notes

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