tert-Butyl acrylate → tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylate

HRID 1690313Notes

Reaction equation

HRID 1690313 reaction equation
Br[C:2]1[CH:3]=[C:4]2[CH2:10][C:9](=[O:11])[NH:8][C:5]2=N[CH:7]=1.[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])(=[O:15])[CH:13]=[CH2:14].[C:21]1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(C(C)C)CC)(C)C>C(#N)CC.CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[O:11]=[C:9]1[CH2:10][C:4]2[C:5](=[CH:21][CH:7]=[C:2](/[CH:14]=[CH:13]/[C:12]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:3]=2)[NH:8]1

Participants

8

Reactant 4

HCID 15458tert-Butyl acrylateHCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 155040625-bromo-1H,2H,3H-pyrrolo(2,3-b)pyridin-2-one

Product 1

HCID 66905345tert-butyl (E)-3-(2-oxo-2,3-dihydro-1H-indol-5-yl)acrylateYield 162.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolventHCID 7854PropionitrileSolvent

Procedure

A solution of 5-bromo-1,3-dihydropyrrolo[2,3-b]pyridin-2-one (2.0 g, 9.49 mmole), tert-butyl acrylate (1.8 g, 14.1 mmole), Pd(OAc)2 (0.32 g, 1.4 mmole), tri-ortho-tolylphosphine (0.57 g, 1.9 mmole), and diisopropylethylamine (4.9 mL, 28.2 mmole) in propionitrile (100 mL) and DMF (10 mL) was heated at reflux overnight. The dark mixture was filtered through celite®, and the filtrate was concentrated. Flash chromatography on silica (9:1 CHCl3/CH3OH containing 5% NH4OH) gave the title compound (0.80 g, 33%) as a light yellow solid. MS (ES) m/e 261 (M+H)+.

Workup

  1. temperatureat reflux overnight
  2. filtrationThe dark mixture was filtered through celite®
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4dc6f2dcbf814ee5a42ed537b70e83be
Source dataset
uspto-grants-2012_04
Patent number
US08153652B2

Reaction notes

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