Water → (5-Bromo-4-chloro-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

HRID 74598Notes

Reaction equation

HRID 74598 reaction equation
CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Br:23][C:24]1[C:25]([Cl:33])=[CH:26][C:27]([C:30]([OH:32])=O)=[N:28][CH:29]=1.[F:34][C:35]1[CH:36]=[C:37]2[C:41](=[CH:42][CH:43]=1)[NH:40][CH2:39][CH2:38]2.O>CN(C=O)C>[Br:23][C:24]1[C:25]([Cl:33])=[CH:26][C:27]([C:30]([N:40]2[C:41]3[C:37](=[CH:36][C:35]([F:34])=[CH:43][CH:42]=3)[CH2:38][CH2:39]2)=[O:32])=[N:28][CH:29]=1

Participants

6

Reactant 4

HCID 962WaterHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-FluoroindolineHCID 583866545-Bromo-4-chloropyridine-2-carboxylic acid

Product 1

HCID 58386444(5-Bromo-4-chloro-pyridin-2-yl)-(5-fluoro-2,3-dihydro-indol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

0.75 mg (2.3 mmol) TBTU were added to 0.50 g (2.1 mmol) 5-bromo-4-chloro-pyridine-2-carboxylic acid, 0.29 g (2.1 mmol) 5-fluoro-2,3-dihydro-1H-indole and 0.62 mL (4.4 mmol) TEA in 11 mL DMF and the mixture was stirred overnight at RT. Then the reaction mixture was combined with water, the precipitate formed was suction filtered and dried.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-ca0196b21ea7422b95abf6325bf9cc88
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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