Methyl Acrylate → HCID 58247920, compound

HRID 339129Notes

Reaction equation

HRID 339129 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH:7]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:6][CH2:5]2.[C:19]([O:23][CH3:24])(=[O:22])[CH:20]=[CH2:21]>C(N(CC)CC)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>[C:14]([O:13][C:12]([NH:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2](/[CH:21]=[CH:20]/[C:19]([O:23][CH3:24])=[O:22])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1)=[O:18])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 2

HCID 7294Methyl AcrylateHCID 58247994tert-butyl (5-bromo-2,3-dihydro-1h-inden-1-yl)carbamate

Product 1

HCID 58247920HCID 58247920, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 80271Tri-o-tolylphosphineCatalystHCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 25 g (80.1 mmol) of tert-butyl (5-bromo-2,3-dihydro-1H-inden-1-yl)carbamate, 975 mg (3.20 mmol) of tris(2-methylphenyl)phosphine, 179 mg (797 μmol) of palladium(II) acetate and 8.9 g (103 mmol) of methyl acrylate in 150 ml of triethylamine was stirred at 150° C. for five hours. The precipitate was filtered off, and chromatographic purification afforded 19 g (59.9 mmol) of methyl (2E)-3-[1-[(tert-butoxycarbonyl)amino]-2,3-dihydro-1H-inden-5-yl]acrylate (75%).

Workup

  1. filtrationThe precipitate was filtered off
  2. customchromatographic purification

Sources & evidence

ORD record
ord-cebcade80b7547c5ac7b1f9b622bb597
Source dataset
uspto-grants-2014_11
Patent number
US08889878B2

Reaction notes

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