N-bromobutanimide → 2-[3-bromo-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 1445075Notes

Reaction equation

HRID 1445075 reaction equation
[Br:1]N1C(=O)CCC1=O.[ClH:9].[F:10][C:11]1[CH:12]=[C:13]([CH:35]=[CH:36][CH:37]=1)[CH2:14][N:15]1[C:19]2=[C:20]([N:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25]3)[N:21]=[CH:22][CH:23]=[C:18]2[CH:17]=[C:16]1[CH3:34]>ClCCl>[ClH:9].[Br:1][C:17]1[C:18]2[C:19](=[C:20]([N:24]3[CH2:33][CH2:32][C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH2:25]3)[N:21]=[CH:22][CH:23]=2)[N:15]([CH2:14][C:13]2[CH:35]=[CH:36][CH:37]=[C:11]([F:10])[CH:12]=2)[C:16]=1[CH3:34]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 67141928HCID 67141928, compound

Product 1

HCID 671420752-[3-bromo-1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 8.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (41 mg, 0.23 mmol) and silica gel (100 mg) were added to a solution of 2-[1-(3-fluorobenzyl)-2-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl]-1,2,3,4-tetrahydroisoquinoline hydrochloride (88 mg, 0.23 mmol) prepared in Example 613 in dichloromethane (2 ml). The reaction mixture was stirred for 1 hour and then filtered. The resulting filtrate was concentrated under reduced pressure. The resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5, v/v). The resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas, and then filtered to give 10 mg of the titled compound as a white solid.

Workup

  1. filtrationfiltered
  2. concentrationThe resulting filtrate was concentrated under reduced pressure
  3. customThe resulting residue was purified with silica gel column chromatography (ethyl acetate/n-hexane=1/5
  4. dissolutionThe resulting product was dissolved in ethyl acetate, saturated with hydrochloric acid gas
  5. filtrationfiltered

Sources & evidence

ORD record
ord-c93b0ddce0de4bf2967fdf63b6b9be21
Source dataset
uspto-grants-2010_02
Patent number
US07662832B2

Reaction notes

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