Dichloromethane → HCID 86593818, compound

HRID 585152Notes

Reaction equation

HRID 585152 reaction equation
[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.C(Cl)[Cl:28]>>[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

Participants

3

Reactant 2

HCID 6344DichloromethaneHCID 69331104HCID 69331104, compound

Product 1

HCID 86593818HCID 86593818, compound

Procedure

To a solution of (S)-3-(5-chloro-2-methoxy-phenyl)-3-fluoro-1-hydroxymethyl-6-trifluoromethyl-1,3-dihydro-indol-2-one ((S)-IV) (64.5 g, 0.166 mol) in CH2Cl2 (700 mL) was added PCI3 (2.0 M in CH2Cl2, 255.0 mL, 0.510 mol) dropwise at 0° C. under N2 over a period of 50 minutes. The resultant mixture was warmed to room temperature 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 minutes. 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). 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).

Workup

  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

Sources & evidence

ORD record
ord-cfe30c1d859c4d47938b77ca651e0f36
Source dataset
uspto-grants-2005_08
Patent number
US06930100B2

Reaction notes

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