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

HRID 985286ノート

反応式

HRID 985286 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-dc3dc53d02bb47339047e1d23d154924
出典データセット
uspto-grants-2005_03
特許番号
US06869962B2

反応ノート

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