Methyl iodide → HCID 86635686, compound

HRID 1020699Notes

Reaction equation

HRID 1020699 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5]([F:24])=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14][CH2:13][C:9]=3[NH:10][C:11]=2[CH:12]=1.I[CH3:26]>CN(C=O)C>[Br:3][C:4]1[C:5]([F:24])=[CH:6][C:7]2[C:8]3[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:14][CH2:13][C:9]=3[N:10]([CH3:26])[C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 579504461,1-Dimethylethyl 7-bromo-8-fluoro-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 86635686HCID 86635686, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% weight dispersion in mineral oil, 150 mg, 3.66 mmol) was added to a solution of tert-butyl 7-bromo-8-fluoro-3,4-dihydro-1H-pyrido[4,3-b]indole-2(5H)-carboxylate (0.9 g, 2.44 mmol) in 20 ml of DMF, and the mixture was stirred for 40 min at ambient temperature. Iodomethane (0.25 mL, 3.66 mmol) was added, and the resulting suspension was stirred for 2 h. The resulting mixture was concentrated under reduced pressure to ⅓ of initial volume and treated with water (20 mL). The resulting precipitate was collected by filtration, sequentially washed with water and diethyl ether and dried under vacuum to afford the title compound (0.75 g, 83%) as a yellow solid: 1H NMR (300 MHz, CDCl3) δ 7.42 (d, J=5.4 Hz, 1H), 7.17 (d, J=9.3 Hz, 1H), 4.45 (br s, 2H), 3.81 (br m, 2H), 3.60 (s, 3H), 2.78 (br m, 2H), 1.52 (s, 9H); ESI MS m/z 383 [M+H]+.

Workup

  1. stirringthe resulting suspension was stirred for 2 h
  2. concentrationThe resulting mixture was concentrated under reduced pressure
  3. additiontreated with water (20 mL)
  4. filtrationThe resulting precipitate was collected by filtration
  5. washsequentially washed with water and diethyl ether
  6. customdried under vacuum

Sources & evidence

ORD record
ord-b3e6b6860a9644a793e583b37c131b74
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

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