Potassium Carbonate → (2-Chloro-pyridin-4-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 1640258Notes

Reaction equation

HRID 1640258 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.Cl.[F:12][C:13]1[C:21]([F:22])=[CH:20][CH:19]=[C:18]2[C:14]=1[CH2:15][CH2:16][NH:17]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:17]2[C:18]3[C:14](=[C:13]([F:12])[C:21]([F:22])=[CH:20][CH:19]=3)[CH2:15][CH2:16]2)=[O:7])[CH:8]=[CH:9][N:10]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2369852-Chloroisonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 447549184,5-Difluoroindoline hydrochloride

Product 1

HCID 58117528(2-Chloro-pyridin-4-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g (3.2 mmol) 2-chloroisonicotinic acid, 0.63 mg (3.3 mmol) 4,5-difluoroindoline-hydrochloride, 0.91 mL (6.5 mmol) TEA and 1.1 g (3.4 mmol) TBTU in 10 mL DMF were stirred overnight at RT. Then the reaction mixture was poured onto 200 mL of 15% potassium carbonate solution, the precipitate formed was suction filtered, washed with water and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. washwashed with water
  4. customdried

Sources & evidence

ORD record
ord-502a81c38aff4c36a91c8178357b894f
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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