Cesium carbonate → HCID 10703244, compound

HRID 2206632Notes

Reaction equation

HRID 2206632 reaction equation
Br[C:2]1([C:11](OC)=O)[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:3]1.CC1(C)[C:20](C)(C)[O:19]B(C=C)O1.[C:26](=[O:29])([O-])[O-].[Cs+].[Cs+].O1CCOC[CH2:33]1.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>[CH:11]([C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:26]([O:19][CH3:20])=[O:29])=[CH:8][CH:7]=[CH:6][CH:5]=2)=[CH2:33]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 52330122-Ethenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolaneHCID 218864351,4-Dioxane--water (1/1)HCID 118364345HCID 118364345, compound

Product 1

HCID 10703244HCID 10703244, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Methyl 2-bromo-1H-indole-carboxylate (100 mg, 0.19 mmol), 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (154 mg, 1 mmol), tetrakis(triphenylphosphine)palladium (116 mg, 0.1 mmol) and cesiumcarbonate (326 mg, 1 mmol) in dioxane/water (20 mL/5 mL) were stirred at room temperature for 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 give methyl 2-vinyl-1H-indole-3-carboxylate as a pale yellow solid (60 mg, 76%) LRMS (M+H+) m/z: calcd 201.1 found 201.

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-5444f3a2c26444d9bf0b32e575f5c0a2
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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