2-Chloroisonicotinic acid → (2-Chloro-pyridin-4-yl)-(5,6-difluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74580Notes

Reaction equation

HRID 74580 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][N:10]=1)[C:5]([OH:7])=O.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][C:20]=1[F:21])[NH:17][CH2:16][CH2:15]2.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[C:20]([F:21])[CH:19]=3)[CH2:15][CH2:16]2)=[O:7])[CH:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 2369852-Chloroisonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 167925945,6-Difluoroindoline

Product 1

HCID 58386704(2-Chloro-pyridin-4-yl)-(5,6-difluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.35 g (2.2 mmol) 2-chloroisonicotinic acid, 0.34 g (2.2 mmol) 5,6-difluoro-2,3-dihydro-1 H-indole, 0.70 mL (5.0 mmol) TEA and 10 mL DMF were mixed with 0.77 g (2.4 mmol) TBTU and stirred for 2 h at RT. The reaction mixture was purified by HPLC. The product fractions were combined and evaporated down.

Workup

  1. customThe reaction mixture was purified by HPLC
  2. customevaporated down

Sources & evidence

ORD record
ord-dc680f7fb7084e5ab8318dbfc433ca41
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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