Dichloromethane → HCID 90046309, compound

HRID 1507582Notes

Reaction equation

HRID 1507582 reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[N:8]2[CH:11]2[CH2:13][CH2:12]2)=[CH:4][C:3]=1[F:17].[OH-].[NH4+:19].ClCCl>CN1C(=O)CCC1.[Cu-]=O>[NH2:19][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([CH3:16])([CH3:15])[C:7](=[O:14])[N:8]2[CH:11]2[CH2:13][CH2:12]2)=[CH:4][C:3]=1[F:17]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 14923Ammonium HydroxideHCID 90046360HCID 90046360, compound

Product 1

HCID 90046309HCID 90046309, compound

Reagents, catalysts & solvents 2

HCID 178419072HCID 178419072, compoundCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 6-bromo-1-cyclopropyl-5-fluoro-3,3-dimethylindolin-2-one (example 36b, 400 mg, 1.34 mmol) in NMP (7 ml) were added ammonium hydroxide (6.3 g, 7 ml, 44.9 mmol) and copper(I) oxide (38.4 mg, 268 μmol). The reaction mixture was heated in a sealed tube to 110° C. for 24 hours and then poured into dichloromethane (20 ml). The organic phase was washed with 1 M aqueous sodium bicarbonate solution and with water, dried over sodium sulfate and concentrated in vacuo. The NMP was removed by kugelrohr distillation. The residue was purified by silica gel chromatography using ethyl acetate/heptane as eluent. The title compound was obtained as off-white crystals (257 mg).

Workup

  1. washThe organic phase was washed with 1 M aqueous sodium bicarbonate solution and with water
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe NMP was removed by kugelrohr distillation
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-ad7defecaf184768879b44b61107c19b
Source dataset
uspto-grants-2015_12
Patent number
US09221816B2

Reaction notes

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