O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate → (2-Chloro-6-methoxypyridin-4-yl)-(5-fluoro-2,3-dihydroindol-1-yl)-methanone

HRID 74550

Reaction equation

HRID 74550 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)[C:5]([OH:7])=O.[F:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH2:18][CH2:17]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:19]2[C:20]3[C:16](=[CH:15][C:14]([F:13])=[CH:22][CH:21]=3)[CH2:17][CH2:18]2)=[O:7])[CH:8]=[C:9]([O:11][CH3:12])[N:10]=1

Participants

5

Reactant 3

HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 27821242-Chloro-6-methoxypyridine-4-carboxylic acid

Product 1

HCID 58386441(2-Chloro-6-methoxypyridin-4-yl)-(5-fluoro-2,3-dihydroindol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.50 g (2.7 mmol) 2-chloro-6-methoxyisonicotinic acid, 0.37 g (2.7 mmol) 5-fluoroindoline and 0.42 mL (3 mmol) TEA were in 10 mL DMF placed. 0.97 g (3.0 mmol) TBTU were added and the reaction mixture was 2 h stirred at RT. The substance was purified by HPLC. The product-containing fractions were combined and freeze-dried.

Workup

  1. customThe substance was purified by HPLC
  2. customfreeze-dried

Sources & evidence

ORD record
ord-2aaf8833422d4f5c929e77143a2dbfe9
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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