Triethylamine → (4-Chloropyridin-2-yl)-(5-fluoro-2,3-dihydroindol-1-yl)-methanone

HRID 74509Notes

Reaction equation

HRID 74509 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][CH2:5]2.[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18](O)=[O:19])[CH:13]=1.C(N(CC)CC)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([C:18]([N:7]2[C:8]3[C:4](=[CH:3][C:2]([F:1])=[CH:10][CH:9]=3)[CH2:5][CH2:6]2)=[O:19])[CH:13]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2308904-Chloropyridine-2-carboxylic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-Fluoroindoline

Product 1

HCID 58386740(4-Chloropyridin-2-yl)-(5-fluoro-2,3-dihydroindol-1-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

174 mg (1.27 mmol) 5-fluoro-2,3-dihydro-1H-indole were added to 200.0 mg (1.27 mmol) 4-chloropyridine-2-carboxylic acid, 351 μL (2.50 mmol) triethylamine and 434.0 mg (1.35 mmol) TBTU in 3 mL DMF. The reaction mixture was stirred overnight at RT. Purification was carried out by preparative HPLC. The product fractions were combined and evaporated down i. vac.

Workup

  1. customPurification
  2. customevaporated down i

Sources & evidence

ORD record
ord-2734c073f2eb46e681607cbaafcd9340
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Reaction notes

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