Methyl Acrylate → HCID 57810466, compound

HRID 1817993Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11].[C:13]([O:17][CH3:18])(=[O:16])[CH:14]=[CH2:15].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(N(CC)CC)C.C(Cl)Cl.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:18][O:17][C:13](=[O:16])/[CH:14]=[CH:15]/[C:2]1[CH:3]=[C:4]([F:12])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[C:7]2[CH3:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a mixture of 7-Bromo-5-fluoro-3-methyl-1H-indole, [which was prepared analogous to I-30, according to the method of Dobbs, A., J. Org. Chem., 66, 638-641 (2001)], (870 mg, 3.8 mmol) and methyl acrylate (819 mg, 9.5 mmol) in triethylamine (4 ml), palladium(II) acetate (112 mg, 0.5 mmol) and tri-o-tolylphosphine (428 mg, 1.42 mmol) was added under argon at rt The reaction mixture was stirred at 100° C. for 3 hrs in a sealed pressure tube and then cooled to rt The reaction mixture was diluted with CH2Cl2 (70 ml), washed with water (3×40 ml), brine, and dried over sodium sulfate. After removal of solvent, the residue purified by column chromatography on silica gel with methanol/dichloromethane as an eluent to give 690 mg of compound I-33 as a solid. 1H-NMR (500 MHz, CDCl3).

Workup

custom[which was prepared analogous to I-30
temperaturecooled to rt The reaction mixture
washwashed with water (3×40 ml), brine
dry with materialdried over sodium sulfate
customAfter removal of solvent
customthe residue purified by column chromatography on silica gel with methanol/dichloromethane as an eluent

Sources & evidence

ORD record: ord-b6984f36306f4f3a95becbd5c2ae8d8c
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07598397B2

Reaction notes

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