Water → HCID 57950435, compound

HRID 930760Notes

Reaction equation

HRID 930760 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[CH2:16][C:15]([CH3:18])([CH3:17])[N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:9]=3[NH:10]2)=[CH:6][CH:5]=1.[CH3:26]I.O>CN(C=O)C>[Br:3][C:4]1[CH:12]=[C:11]2[C:7]([C:8]3[CH2:16][C:15]([CH3:17])([CH3:18])[N:14]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:13][C:9]=3[N:10]2[CH3:26])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57950388HCID 57950388, compound

Product 1

HCID 57950435HCID 57950435, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

NaH (60% dispersion in oil, 42 mg, 1.1 mmol) was added to a solution of tert-butyl 7-bromo-3,3-dimethyl-3,4-dihydro-1H-pyrido[3,4-b]indole-2(9H)-carboxylate (200 mg, 0.528 mmol) in DMF (10 mL) under N2, and the resulting suspension was stirred at 25° C. for 30 min. MeI (0.05 mL, 0.8 mmol) was added to the suspension, and the resulting suspension was stirred at 25° C. for 1 h. H2O was added, and the resulting solid was collected by filtration. Flash chromatography (silica gel, hexanes/(1:1 EtOAc/hexanes), 100:0 to 0:100) afforded the title compound (145 mg, 70%) as a white solid: 1H NMR (300 MHz, CDCl3) δ 7.43 (d, J=1.5 Hz, 1H), 7.30 (d, J=8.3 Hz, 1H), 7.18 (dd, J=8.3, 1.5 Hz, 1H), 4.62 (s, 2H), 3.61 (s, 3H), 2.77 (s, 2H), 1.52 (s, 6H), 1.49 (s, 9H).

Workup

  1. stirringthe resulting suspension was stirred at 25° C. for 1 h
  2. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-aa96ceaff9154e90ba3456e44562c5d5
Source dataset
uspto-grants-2016_03
Patent number
US09296743B2

Reaction notes

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