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Cesium carbonate → Methyl 2-phenyl-1H-indole-3-carboxylate

HRID 2206629
Notes
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Reaction equation

HRID 2206629 reaction equation
Br[C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:15]1([C:2]2[NH:3][C:4]3[C:9]([C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=3)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 89739680HCID 89739680, compound

Product 1

HCID 11379731Methyl 2-phenyl-1H-indole-3-carboxylateYield 80.6%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 21886435
1,4-Dioxane--water (1/1)
Solvent

Procedure

Methyl 2-bromo-1H-indole-3-carboxylate (200 mg, 0.79 mmol), phenylboronic acid (122 mg, 1 mmol), tetrakis(triphenylphosphine)palladium (231 mg, 0.2 mmol) and cesiumcarbonate (652 mg, 2 mmol) in dioxane/water (20 mL/5 mL) were stirred at room temperature 15 hours. Filterated the solid and the solvent was concentrated in vacuum. The resulted residue was purified by silica gel column (ethyl acetate: petroleum ether=1:2) to obtain methyl 2-phenyl-1H-indole-3-carboxylate as a pale yellow solid (160 mg, 80%) LRMS (M+H+) m/z: calcd 251.1 found 251.

Workup

  1. concentrationthe solvent was concentrated in vacuum
  2. customThe resulted residue was purified by silica gel column (ethyl acetate: petroleum ether=1:2)

Sources & evidence

ORD record
ord-e2c99d600056454697ab1dc510ec2f42
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371331B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes