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

HRID 2059974Notes

Reaction equation

HRID 2059974 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl:23][C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([O:33][CH3:34])[N:32]=1)[C:27]([OH:29])=O.[F:35][C:36]1[CH:37]=[C:38]2[C:42](=[CH:43][CH:44]=1)[NH:41][CH2:40][CH2:39]2.C(N(CC)CC)C>CN(C=O)C>[Cl:23][C:24]1[CH:25]=[C:26]([C:27]([N:41]2[C:42]3[C:38](=[CH:37][C:36]([F:35])=[CH:44][CH:43]=3)[CH2:39][CH2:40]2)=[O:29])[CH:30]=[C:31]([O:33][CH3:34])[N:32]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 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

0.965 g (3.00 mmol) TBTU was added at RT to 0.500 g (2.67 mmol) 2-chloro-6-methoxyisonicotinic acid, 0.366 g (2.67 mmol) 5-fluoroindoline and 0.421 mL (3.00 mmol) triethylamine in 10.0 mL DMF. The mixture was stirred for 2 h at RT and then purified by preparative HPLC. The fractions containing the product were combined and evaporated down i. vac.

Workup

  1. custompurified by preparative HPLC
  2. additionThe fractions containing the product
  3. customevaporated down i

Sources & evidence

ORD record
ord-4a9abb9d2279475e90dbd8dd1ba54ebd
Source dataset
uspto-grants-2012_10
Patent number
US08278336B2

Reaction notes

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