4-Chloropyridine-2-carboxylic acid → (4-Chloro-pyridin-2-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74548Notes

Reaction equation

HRID 74548 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[F:34][C:35]1[C:43]([F:44])=[CH:42][CH:41]=[C:40]2[C:36]=1[CH2:37][CH2:38][NH:39]2>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([N:39]2[C:40]3[C:36](=[C:35]([F:34])[C:43]([F:44])=[CH:42][CH:41]=3)[CH2:37][CH2:38]2)=[O:10])[CH:3]=1

Participants

5

Reactant 3

HCID 2308904-Chloropyridine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 447549184,5-Difluoroindoline hydrochloride

Product 1

HCID 58386701(4-Chloro-pyridin-2-yl)-(4,5-difluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g (3.2 mmol) 4-chloropicolinic acid, 1.1 g (3.4 mmol) TBTU and 0.91 mL (6.5 mmol) TEA were placed in 10 mL DMF. 0.63 g (3.3 mmol) 4,5-difluoroindoline hydrochloride were added. The reaction mixture was stirred overnight at RT and then extracted successively with a 15% potassium carbonate solution, water, a 1M HCl solution and EtOAc. The organic phase was dried, filtered and concentrated to dryness by rotary evaporation. The residue was stirred with diisopropylether and the undissolved solid was suction filtered and dried.

Workup

  1. extractionextracted successively with a 15% potassium carbonate solution, water
  2. customThe organic phase was dried
  3. filtrationfiltered
  4. concentrationconcentrated to dryness by rotary evaporation
  5. stirringThe residue was stirred with diisopropylether
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-e7715b4c41a841ddbe40092327e7cbb0
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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