1H-Indole-2-carboxylic acid, 1-methyl- → 1-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamide

HRID 2390656Notes

Reaction equation

HRID 2390656 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]([OH:19])=O.[CH3:20][C:21]1([CH3:35])[C:25]([CH3:27])([CH3:26])[O:24][B:23]([C:28]2[CH:34]=[CH:33][C:31]([NH2:32])=[CH:30][CH:29]=2)[O:22]1.C(N(C(C)C)CC)(C)C>CN(C)C=O.ClCCl>[CH3:7][N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:17]([NH:32][C:31]1[CH:30]=[CH:29][C:28]([B:23]2[O:24][C:25]([CH3:27])([CH3:26])[C:21]([CH3:35])([CH3:20])[O:22]2)=[CH:34][CH:33]=1)=[O:19]

Participants

7

Reactant 4

HCID 276951H-Indole-2-carboxylic acid, 1-methyl-HCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 27346204-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

Product 1

HCID 184505431-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-1H-indole-2-carboxamideYield 70.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A mixture of oxalyl chloride (0.35 mL) and dimethylformamide (1 drop) was added to a solution of 1-methyl-1H-2-indolecarboxylic acid (440 mg, 2.51 mmol) in dichloromethane (10 mL). After one hour the mixture was evaporated, dissolved in dichloromethane (10 mL), and added to a mixture of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (500 mg, 2.28 mmol) and diisopropylethylamine (0.35 mL) in dichloromethane (10 mL). After 16 hours the mixture was washed with water (10 mL), dried (MgSO4), filtered, concentrated, and purified by flash column chromatography to provide the desired product (600 mg, 1.60 mmol) after lyophilization: MS m/e 377.4 (M+H)+.

Workup

  1. customAfter one hour the mixture was evaporated
  2. dissolutiondissolved in dichloromethane (10 mL)
  3. washAfter 16 hours the mixture was washed with water (10 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography

Sources & evidence

ORD record
ord-436165f0a66c4d289aa2d7c85fc3ed1d
Source dataset
uspto-grants-2012_09
Patent number
US08273736B2

Reaction notes

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