Triphenylphosphine → 6-Methoxy-2-trifluoromethyl-1H-indole-3-carboxylic acid ethyl ester

HRID 1825169Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[C:6]([NH:11][C:12]1[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=1I)[C:7]([F:10])([F:9])[F:8])[CH3:2].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])(O)=O.[Na+].CCOC(C)=O.O>CN(C=O)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:1]([O:3][C:4]([C:5]1[C:13]2[C:12](=[CH:17][C:16]([O:18][CH3:19])=[CH:15][CH:14]=2)[NH:11][C:6]=1[C:7]([F:10])([F:9])[F:8])=[O:21])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 4,4,4-trifluoro-3-(2-iodo-5-methoxy-phenylamino)-but-2-enoic acid ethyl ester 76c (0.5 g, 1.2 mmole), Pd(OAc)2 (22.4 mg, 0.1 mmole), PPh3 (52.5 mg, 0.2 mmole) and NaHCO3 (505 mg, 6 mmole) in 5 ml DMF was heated at 120° C. under argon for 24 hours and cooled to room temperature. The mixture was poured into EtOAc/water and washed with brine. The organic layer was dried over Na2SO4 and concentrated under rot vap. The residue was purified by column chromatography to give 217 mg product (63% yield). 1H NMR. (300 MHz, CD3OD) δ 8.00 (1H, d, J=9.0 Hz), 6.96 (1H, d, J=2.0 Hz), 6.90 (1H, dd, J=2.0, 9.0 Hz), 4.37 (2H, m), 3.84 (3H, s), 1.40 (3H, m).

Workup

temperaturecooled to room temperature
washwashed with brine
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under rot vap
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-c4cb354358fa43bcb3e36f2b2babc336
Source dataset: uspto-grants-2006_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07045528B2

Reaction notes

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