Pyridine → 1-(5-Bromo-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanone

HRID 1475318Notes

Reaction equation

HRID 1475318 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH2:6][C:5]2([CH3:12])[CH3:11].N1C=CC=CC=1.[C:19](OC(=O)C)(=[O:21])[CH3:20]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:19](=[O:21])[CH3:20])[CH2:6][C:5]2([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 111837195-bromo-3,3-dimethyl-2,3-dihydro-1H-indole

Product 1

HCID 161154361-(5-Bromo-3,3-dimethyl-2,3-dihydro-indol-1-yl)-ethanoneYield 94.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-bromo-3,3-dimethyl-2,3-dihydro-1H-indole (1.6 g, 7.1 mmol) in DCM (40 mL) and pyridine (1.1 mL, 14.2 mmol) was added acetic anhydride (1 mL, 11 mmol). The reaction was stirred at room temperature overnight, then solvent was removed in vacuo and the residue partitioned between water and saturated aqueous NH4Cl. The organic phase was separated, dried (MgSO4), filtered and concentrated to give the title compound (1.8 g), used without further purification. Analytical data were consistent with those reported in Preparation 61.

Workup

  1. customsolvent was removed in vacuo
  2. customthe residue partitioned between water and saturated aqueous NH4Cl
  3. customThe organic phase was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-919597d1e7bd49e0a45b83c67da3eeaa
Source dataset
uspto-grants-2015_04
Patent number
US09018214B2

Reaction notes

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