Phenyl chloroformate → Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamate

HRID 1035841Notes

Reaction equation

HRID 1035841 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[NH2:11][C:12]1([C:38]2[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=2)[C:20]2[C:15](=[CH:16][C:17]([F:23])=[C:18]([C:21]#[N:22])[CH:19]=2)[N:14]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=2[O:35][CH3:36])(=[O:26])=[O:25])[C:13]1=[O:37]>N1C=CC=CC=1>[C:21]([C:18]1[CH:19]=[C:20]2[C:15](=[CH:16][C:17]=1[F:23])[N:14]([S:24]([C:27]1[CH:32]=[CH:31][C:30]([O:33][CH3:34])=[CH:29][C:28]=1[O:35][CH3:36])(=[O:25])=[O:26])[C:13](=[O:37])[C:12]2([NH:11][C:2](=[O:3])[O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[C:38]1[C:39]([O:44][CH2:45][CH3:46])=[N:40][CH:41]=[CH:42][CH:43]=1)#[N:22]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 670877293-Amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile

Product 1

HCID 86725451Phenyl [5-cyano-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indol-3-yl]carbamateYield 71.9%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

61 μl (0.49 mmol) of phenyl chloroformate were slowly added dropwise to a solution, cooled to 0° C., of 226 mg (0.44 mmol) of 3-amino-1-(2,4-dimethoxyphenylsulfonyl)-3-(2-ethoxypyridin-3-yl)-6-fluoro-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile in 4 ml of pyridine. After 5 minutes, the solvent was evaporated. The residue was mixed with 20 ml of water and extracted with diethyl ether (2×). The organic phase was washed with water and saturated sodium chloride solution, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate). 200 mg of the title compound were obtained.

Workup

  1. customthe solvent was evaporated
  2. additionThe residue was mixed with 20 ml of water
  3. extractionextracted with diethyl ether (2×)
  4. washThe organic phase was washed with water and saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (Redisep cartridge, mobile phase gradient from 0 to 5% methanol in ethyl acetate)

Sources & evidence

ORD record
ord-8fbcccf893684f24bb3ab7a972a6b210
Source dataset
uspto-grants-2013_10
Patent number
US08546401B2

Reaction notes

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