Potassium Carbonate → (R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl ester

HRID 2175169Notes

Reaction equation

HRID 2175169 reaction equation
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:17]2=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=[C:16]2[NH:15][C:14]1=[O:23])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:2].C([O-])([O-])=O.[K+].[K+].[I-].[CH3:32][N:33]1[C:41]2[C:36](=[C:37]([CH3:42])[CH:38]=[CH:39][CH:40]=2)[C:35]([CH2:43][N+](C)(C)C)=[CH:34]1>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C@@H:6]([N:13]1[C:17]2=[N:18][C:19]([CH3:22])=[CH:20][CH:21]=[C:16]2[N:15]([CH2:43][C:35]2[C:36]3[C:41](=[CH:40][CH:39]=[CH:38][C:37]=3[CH3:42])[N:33]([CH3:32])[CH:34]=2)[C:14]1=[O:23])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 17836486((1,4-Dimethylindole-3-yl)methyl)trimethylammonium iodideHCID 58497418(R)-3-(5-Methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester

Product 1

HCID 58497460(R)-3-[1-(1,4-Dimethyl-1H-indol-3-ylmethyl)-5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl]-3-phenyl-propionic acid ethyl esterYield 54%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (R)-3-(5-methyl-2-oxo-1,2-dihydro-imidazo[4,5-b]pyridin-3-yl)-3-phenyl-propionic acid ethyl ester (250 mg, 0.77 mmol) in DMF (5 mL) were added K2CO3 (212 mg, 1.54 mmol) and (1,4-dimethyl-1H-indol-3-ylmethyl)-trimethyl-ammonium iodide (397 mg, 1.15 mmol). The reaction mixture was heated to 60° C. for 48 hours. The reaction mixture was then diluted with ethyl acetate and washed with water (×4). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel preparative TLC using 98:2 CH2Cl2:MeOH as an eluent to afford 200 mg (54%) of the title compound.

Workup

  1. washwashed with water (×4)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel preparative TLC

Sources & evidence

ORD record
ord-922d02ece8ea4a09a4e7e7eba2d1f368
Source dataset
uspto-grants-2015_06
Patent number
US09062056B2

Reaction notes

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