Diisopropylethylamine → 5-bromo-1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indole

HRID 1909913Notes

Reaction equation

HRID 1909913 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[Br:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[NH:52][CH2:51][CH2:50]2>CN(C)C=O>[Br:46][C:47]1[CH:48]=[C:49]2[C:53](=[CH:54][CH:55]=1)[N:52]([C:10](=[O:12])[CH2:9][C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[F:1])[CH2:51][CH2:50]2

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 5228232,5-Difluorophenylacetic acidHCID 34115665-BromoindolineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 668238625-bromo-1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indoleYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (2,5-difluorophenyl)acetic acid (0.869 g, 5.05 mmol) and HATU (2.112 g, 5.55 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added Hunig's base (0.882 mL, 5.05 mmol), and the resulting mixture was stirred for 15 minutes at room temperature. 5-bromo-2,3-dihydro-1H-indole (1 g, 5.05 mmol) was added, and the reaction mixture was stirred at room temperature for 1 hour. The mixture was poured onto water, and the resulting aqueous mixture was filtered to afford 5-bromo-1-[(2,5-difluorophenyl)acetyl]-2,3-dihydro-1H-indole (1.6 g) as a tan solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 1 hour
  2. additionThe mixture was poured onto water
  3. filtrationthe resulting aqueous mixture was filtered

Sources & evidence

ORD record
ord-df83c659905a4334ab2fb916102e4acb
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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