4-Chloropyridine-2-carboxylic acid → HCID 58386653, compound

HRID 74582

Reaction equation

HRID 74582 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.[F:11][C:12]1[CH:13]=[C:14]2[C:18](=[CH:19][CH:20]=1)[NH:17][CH2:16][C:15]2([CH3:22])[CH3:21].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:7]=[CH:6][N:5]=[C:4]([C:8]([N:17]2[C:18]3[C:14](=[CH:13][C:12]([F:11])=[CH:20][CH:19]=3)[C:15]([CH3:22])([CH3:21])[CH2:16]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 21712575HCID 21712575, compound

Product 1

HCID 58386653HCID 58386653, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.17 g (1.1 mmol) 4-chloro-pyridine-2-carboxylic acid, 0.18 g (1.1 mmol) 5-fluoro-3,3-dimethyl-2,3-dihydro-1H-indole, 0.28 mL (2.0 mmol) TEA and 3.0 mL DMF were combined with 0.39 g (1.2 mmol) TBTU and stirred overnight 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-9a0703c2e67a45d0a715f72ec86fc841
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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