Sodium hydride → 2,3,4,5-Tetrahydro-5-methyl-2-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-one

HRID 2379142Notes

Reaction equation

HRID 2379142 reaction equation
[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:15])[NH:12][CH2:13][CH2:14][C:3]1=2.[H-].[Na+].[H][H].Cl[CH2:21][C:22]1[N:23]=[CH:24][N:25]([C:27]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH:26]=1>CN(C=O)C.C1COCC1.CCCCCC.O>[CH3:1][N:2]1[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]2[C:11](=[O:15])[N:12]([CH2:21][C:22]3[N:23]=[CH:24][N:25]([C:27]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=4)[C:40]4[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=4)[CH:26]=3)[CH2:13][CH2:14][C:3]1=2

Participants

9

Reactant 4

HCID 24758Sodium hydrideHCID 27631764-(Chloromethyl)-1-trityl-1H-imidazoleHCID 117902131H-Pyrido(4,3-b)indol-1-one, 2,3,4,5-tetrahydro-5-methyl-HCID 178418361HCID 178418361, compound

Product 1

HCID 156163312,3,4,5-Tetrahydro-5-methyl-2-[[1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-1H-pyrido[4,3-b]indol-1-oneYield 47.9%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

A mixture of 2,3,4,5-tetrahydro-5-methyl-1H-pyrido[4,3-b]indol-1-one (0.3 g) and sodium hydride (80% dispersion in oil; 0.05 g) in dry DMF (5 ml) was stirred under nitrogen at 50° until hydrogen evolution ceased (ca. 0.5 h). The mixture was cooled to 40° and a solution of 4-(chloromethyl)-1-(triphenylmethyl)-1H-imidazole (0.53 g) in dry THF (3 ml) was added. The mixture was stirred at 40° to 23° over 2 h, poured into water (100 ml) and extracted with dichloromethane (3×100 ml). The dried organic phase was evaporated to give a semi-solid which was purified by FCC eluting with dichloromethane:ethyl acetate:triethylamine (50:50:1) to give a solid. This was slurried in hexane and filtered to give the title compound (0.37 g), m.p. 205°-210° (decomp.).

Workup

  1. custom(ca. 0.5 h)
  2. temperatureThe mixture was cooled to 40°
  3. extractionextracted with dichloromethane (3×100 ml)
  4. customThe dried organic phase was evaporated
  5. customto give a semi-solid which
  6. customwas purified by FCC
  7. washeluting with dichloromethane:ethyl acetate:triethylamine (50:50:1)
  8. customto give a solid
  9. filtrationfiltered

Sources & evidence

ORD record
ord-7b54afb62d124d29bff46ed4c2ec77ac
Source dataset
uspto-grants-1994_11
Patent number
US05360800

Reaction notes

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