Phosphorus trichloride → HCID 86593818、化合物

HRID 1375726ノート

反応式

HRID 1375726 の反応式
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C@@:8]2([F:24])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21]O)[C:9]2=[O:23])[CH:7]=1.P(Cl)(Cl)[Cl:28]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:25][CH3:26])=[C:6]([C@@:8]2([F:24])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:19])([F:20])[F:18])=[CH:14][CH:15]=3)[N:10]([CH2:21][Cl:28])[C:9]2=[O:23])[CH:7]=1

参加物

4

反応物 2

HCID 24387Phosphorus trichlorideHCID 69331104HCID 69331104、化合物

生成物 1

HCID 86593818HCID 86593818、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (S)-3-(5-chloro-2-methoxyphenyl)-1-(hydroxymethyl)-3-fluoro-6-(trifluoromethyl)indolin-2-one ((S)-VI) (64.5 g, 0.166 mol) in CH2Cl2 (700 mL) was added PCl3 (2.0 M in CH2Cl2, 255.0 mL, 0.510 mol) dropwise at 0° C. under N2 over a period of 50 min. The resultant mixture was warmed to rt. and the stirring continued overnight (16 h). The mixture was quenched with ice at 0° C. and the resultant mixture was stirred vigorously for 30 min. The organic layer was separated and the aqueous layer was washed with CH2Cl2. The combined organic layer was washed with brine and dried over Na2SO4. Chromatography (silica gel, EtOAc/Hexanes) provided the title compound as a white dry foam (42.0 g, 62% yield). LC/MS m/e: (no molecular ion), 97% purity. 1H NMR (CDCl3): δ 3.55 (s, 3H), 5.39 (d, J=10.5 Hz, 1H), 5.95 (d, J=11.0 Hz, 1H), 6.76 (dd, J=1.5, 9.0 Hz, 1H), 7.28 (m, 2H), 7.35 (dd, J=1.5, 9.0 Hz, 1H), 7.40 (d, J=8.0 Hz, 1H), 7.78 (dd, J=1.0, 2.5 Hz, 1H).

後処理

  1. customthe stirring continued overnight (16 h)
  2. customThe mixture was quenched with ice at 0° C.
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with CH2Cl2
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over Na2SO4

出典と根拠

ORDレコード
ord-8d3dd353ec33434f9a32d45195bfb217
出典データセット
uspto-grants-2007_01
特許番号
US07169803B2

反応ノート

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