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

HRID 985286노트

반응식

HRID 985286 반응식
[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]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 22728543Water ethylacetateHCID 693678724,4,4-Trifluoro-3-(2-iodo-5-methoxy-phenylamino)-but-2-enoic acid ethyl ester

생성물 1

HCID 207678756-Methoxy-2-trifluoromethyl-1H-indole-3-carboxylic acid ethyl ester수율 63%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

반응 조건

온도
120 °C

실험 절차

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) δ8.00 (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).

후처리

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

출처 및 근거

ORD 기록
ord-dc3dc53d02bb47339047e1d23d154924
출처 데이터셋
uspto-grants-2005_03
특허 번호
US06869962B2

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