Phenylacetic Acid → 5-bromo-1-(phenylacetyl)-2,3-dihydro-1H-indole

HRID 1909912Notes

Reaction equation

HRID 1909912 reaction equation
[C:1]1([CH2:7][C:8]([OH:10])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.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:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[NH:50][CH2:49][CH2:48]2>CN(C)C=O>[Br:44][C:45]1[CH:46]=[C:47]2[C:51](=[CH:52][CH:53]=1)[N:50]([C:8](=[O:10])[CH2:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[CH2:49][CH2:48]2

Participants

6

Reactant 4

HCID 999Phenylacetic AcidHCID 81531DiisopropylethylamineHCID 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 668241055-bromo-1-(phenylacetyl)-2,3-dihydro-1H-indoleYield 77.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of phenylacetic acid (0.687 g, 5.05 mmol) and HATU (2.112 g, 5.55 mmol) in N,N-Dimethylformamide (DMF) (5 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 overnight. The reaction was poured onto water, and the resulting precipitate was filtered and air dried to afford the 5-bromo-1-(phenylacetyl)-2,3-dihydro-1 H-indole (1.24 g) as a tan solid.

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. additionThe reaction was poured onto water
  3. filtrationthe resulting precipitate was filtered
  4. customair dried

Sources & evidence

ORD record
ord-8620f4fe7e6843f4b1d8864f4d6850e3
Source dataset
uspto-grants-2013_12
Patent number
US08598156B2

Reaction notes

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