Phosphorus oxychloride → HCID 117871991, compound

HRID 1477151Notes

Reaction equation

HRID 1477151 reaction equation
P(Cl)(Cl)(Cl)=O.[C:6]([O:10][C:11]([N:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]([CH3:23])([CH3:22])[CH:14]1[C:24](O)=[O:25])=[O:12])([CH3:9])([CH3:8])[CH3:7].[F:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:29]=1[NH2:30]>N1C=CC=CC=1.O>[F:27][C:28]1[CH:34]=[CH:33][CH:32]=[C:31]([F:35])[C:29]=1[NH:30][C:24]([CH:14]1[C:15]([CH3:22])([CH3:23])[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:13]1[C:11]([O:10][C:6]([CH3:9])([CH3:7])[CH3:8])=[O:12])=[O:25]

Participants

6

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 796472,6-DifluoroanilineHCID 117871133HCID 117871133, compound

Product 1

HCID 117871991HCID 117871991, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

Phosphorus oxychloride (74.0 mg, 0.045 mL, 483 μmol, Eq: 2.2) was added dropwise to a solution of 1-(tert-butoxycarbonyl)-3,3-dimethylindoline-2-carboxylic acid (64 mg, 220 μmol, Eq: 1.00) and 2,6-difluoroaniline (54.0 mg, 0.045 mL, 418 μmol, Eq: 1.9) in pyridine (1 mL) and the resulting dark yellow suspension stirred at rt overnight. The reaction mixture was diluted with water (10 mL) and extracted with EtOAc (2×10 mL). The combined organic layers were washed with water (10 mL), 0.1 M aqueous HCl (10 mL) and brine (5 mL) and concentrated in vacuo to give tert-butyl 2-(2,6-difluorophenylcarbamoyl)-3,3-dimethylindoline-1-carboxylate as a white solid (42 mg).

Workup

  1. extractionextracted with EtOAc (2×10 mL)
  2. washThe combined organic layers were washed with water (10 mL), 0.1 M aqueous HCl (10 mL) and brine (5 mL)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-fe7d18e0b53a42d392a7db619ea6db48
Source dataset
uspto-grants-2016_08
Patent number
US09403768B2

Reaction notes

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