Benzyl Bromide → HCID 57559153, compound

HRID 37967Notes

Reaction equation

HRID 37967 reaction equation
[H-].[Na+].[CH2:3]1[C:16]2[C:15]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[NH:9][C:8]=2[C:7]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:6][NH:5][CH2:4]1.[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.[Cl-].[NH4+]>CN(C=O)C>[CH2:20]([O:19][C:17]([C:7]1[C:8]2[NH:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:16]=2[CH2:3][CH2:4][N:5]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:6]=1)=[O:18])[CH3:21]

Participants

6

Reactant 4

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57467979Ethyl 1,2,3,6-tetrahydroazepino[4,5-B]indole-5-carboxylate

Product 1

HCID 57559153HCID 57559153, compoundYield 60.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in mineral oil, 320 mg, 8 mmol) was added to a stirred solution of ethyl 1,2,3,6-tetrahydroazepino[4,5-b]indole-5-carboxylate (520 mg, 2 mmol) in anhydrous DMF (8 mL) at 0° C. under nitrogen, and the resulting mixture was stirred at ambient temperature for 30 minutes. Benzyl bromide (345 mg, 2 mmol) was then added dropwise to the above mixture at 0° C. The resulting mixture was stirred at ambient temperature for 6 hours. Ammonium chloride solution was added carefully to quench the reaction at 0° C. The mixture was extracted with DCM. The combined extracts were washed with saturated ammonium chloride solution, water and brine, dried over sodium sulfate, and evaporated in vacuo to give a brown oil, which was purified by chromatography on silica gel eluting with EtOAc-Hexane (5:95) to give the title compound (421 mg); 1H-NMR (CDCl3): δ 10.53 (1H, s), 7.96 (1H, s), 7.41-7.25 (7H, m), 7.08-6.99 (2H, m), 4.57 (2H, s), 4.33-4.27 (2H, q), 3.48 (2H, m), 3.01 (2H, m), 1.36 (3H, t); MS (ES): 347 (MH+).

Workup

  1. stirringThe resulting mixture was stirred at ambient temperature for 6 hours
  2. customto quench
  3. customthe reaction at 0° C
  4. extractionThe mixture was extracted with DCM
  5. washThe combined extracts were washed with saturated ammonium chloride solution, water and brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto give a brown oil, which
  9. customwas purified by chromatography on silica gel eluting with EtOAc-Hexane (5:95)

Sources & evidence

ORD record
ord-c61825d0b8554b189473b2b4900ac307
Source dataset
uspto-grants-2013_09
Patent number
US08524704B2

Reaction notes

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