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

HRID 74508

Reaction equation

HRID 74508 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:13]=[C:14]([CH:18]=[CH:19][N:20]=1)[C:15](O)=[O:16].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:13]=[C:14]([C:15]([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:16])[CH:18]=[CH:19][N:20]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 2369852-Chloroisonicotinic acidHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 27744635-Fluoroindoline

Product 1

HCID 58386590(2-Chloropyridin-4-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 198 mg (1.26 mmol) 2-chloroisonicotinic acid, 351 μL (2.50 mmol) triethylamine and 434 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-5d720ad4a5af4249b03846e9b4bcd2f1
Source dataset
uspto-grants-2014_09
Patent number
US08829006B2

Linked notes

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