Methanol → HCID 67309984, compound

HRID 1401462Notes

Reaction equation

HRID 1401462 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]3[CH2:13][CH2:14][N:15]([CH3:17])[CH2:16][C:7]=3[C:6]=2[CH:5]=1.[CH2:18](Br)[CH:19]=[CH2:20].CO>CN(C=O)C>[CH2:20]([N:9]1[C:10]2[CH:11]=[CH:12][C:4]([Cl:3])=[CH:5][C:6]=2[C:7]2[CH2:16][N:15]([CH3:17])[CH2:14][CH2:13][C:8]1=2)[CH:19]=[CH2:18]

Participants

6

Reactant 4

HCID 887MethanolHCID 7841Allyl bromideHCID 196158-chloro-2-methyl-1H,2H,3H,4H,5H-pyrido(4,3-b)indoleHCID 24758Sodium hydride

Product 1

HCID 67309984HCID 67309984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a suspension of NaH (60% dispersion in oil, 240 mg, 6 mmol) in DMF (15 mL) at 0° C. was added 8-chloro-2-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (1.1 g, 5 mmol) and the reaction mixture was stirred at 0° C. for 30 min, followed by addition of allyl bromide (0.51 mL, 6 mmol). The reaction mixture was allowed to warm to and was stirred at 25° C. for 3 h. MeOH was added and the reaction mixture was evaporated to dryness. The residue was purified by flash chromatography on silica gel using MeOH-DCM gradient. 1H NMR (DMSO-d6) δ (ppm): 7.53 (s, 1H), 7.47 (d, 1H), 7.15 (d, 1H), 5.94 (m, 1H), 5.1 (m, 1H), 4.83 (m, 1H), 4.78 (s, 2H), 4.25 (s, 2H), 3.44 (s, 2H), 3.02 (s, 2H), 2.86 (s, 3H).

Workup

  1. temperatureto warm to and
  2. stirringwas stirred at 25° C. for 3 h
  3. customthe reaction mixture was evaporated to dryness
  4. customThe residue was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-32cd8b5e21c74531a9b3f51c73ec5f33
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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