Methyl iodide → HCID 57950340, compound

HRID 1020704Notes

Reaction equation

HRID 1020704 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:13][C:9]=3[NH:10]2)=[CH:6][C:5]=1[F:24].[CH3:25]I>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[CH2:16][CH2:15][N:14]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:13][C:9]=3[N:10]2[CH3:25])=[CH:6][C:5]=1[F:24]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57950329tert-Butyl 7-bromo-6-fluoro-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate

Product 1

HCID 57950340HCID 57950340, compoundYield 91.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% weight dispersion in mineral oil, 25 mg, 0.60 mmol) was added to a solution of tert-butyl 7-bromo-6-fluoro-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (150 mg, 0.40 mmol) in DMF (10 mL) at room temperature under N2 and stirred for 1 h at ambient temperature. Methyl iodide (230 mg, 0.16 mL, 0.60 mmol) was added, and the reaction mixture was stirred for 1 h. The resulting mixture was concentrated under reduced pressure to approximately ⅓ of initial volume and treated with water (20 mL). The resulting precipitate was collected by filtration, washed with water and diethyl ether and dried under vacuum to afford the title compound (140 mg, 91%) as a yellow powder: ESI MS m/z 383 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred for 1 h
  2. concentrationThe resulting mixture was concentrated under reduced pressure to approximately ⅓ of initial volume
  3. additiontreated with water (20 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washwashed with water and diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-2b19c909fd9c44f69052fbaabeaf4256
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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