1H-imidazole-2-carbaldehyde → (RS)-5-Chloro-1-(1H-imidazol-2-ylmethyl)-2-methyl-2,3-dihydro-1H-indole

HRID 1172991Notes

Reaction equation

HRID 1172991 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]([CH3:11])[CH2:5]2.[NH:12]1[CH:16]=[CH:15][N:14]=[C:13]1[CH:17]=O.C([BH3-])#N.[Na+]>CO.[Cl-].[Zn+2].[Cl-]>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:17][C:13]1[NH:12][CH:16]=[CH:15][N:14]=1)[CH:6]([CH3:11])[CH2:5]2

Participants

6

Reactant 3

HCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 595568185-chloro-2-methyl-2,3-dihydro-1H-indole

Product 1

HCID 59556814(RS)-5-Chloro-1-(1H-imidazol-2-ylmethyl)-2-methyl-2,3-dihydro-1H-indole

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalystHCID 887MethanolSolvent

Procedure

Prepared analogously to Example 1, from 5-chloro-2-methyl-2,3-dihydro-1H-indole, imidazole-2-carboxaldehyde, zinc chloride and sodium cyanoborohydride in methanol. MS (ISP): 250.1 ([{37Cl}M+H]+), 248.2 ([{35Cl}M+H]+).

Sources & evidence

ORD record
ord-c0ba9ad74fbc4fe3867189831552b0ac
Source dataset
uspto-grants-2010_11
Patent number
US07834044B2

Reaction notes

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