Acetic Acid → HCID 86602967, compound

HRID 2067945Notes

Reaction equation

HRID 2067945 reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([CH3:24])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]([F:23])([F:22])[F:21])[CH:13]=2)[C:10]=1[CH3:11])=[O:5])C.[Cl:25][C:26]1[CH:31]=[C:30]([CH3:32])[CH:29]=[CH:28][N:27]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C(O)(=O)C>C1(C)C=CC=CC=1>[Cl:25][C:26]1[CH:31]=[C:30]([CH2:32][C:4]([C:6]2[N:7]=[C:8]([CH3:24])[N:9]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([C:20]([F:21])([F:23])[F:22])[CH:13]=3)[C:10]=2[CH3:11])=[O:5])[CH:29]=[CH:28][N:27]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 772482-Chloro-4-methylpyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 68710756HCID 68710756, compound

Product 1

HCID 86602967HCID 86602967, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Conditions

Temperature
0 °C

Procedure

1-(4-Methoxy-3-trifluoromethyl-phenyl)-2,5-dimethyl-1H-imidazole-4-carboxylic acid ethyl ester (0.8 g, 2.3 mmol) and 2-chloro-4-methylpyridine (0.36 g, 2.8 mmol) were dissolved in 10 mL toluene. This solution was dropped to a cold (0° C.) mixture of potassium bis(trimethylsilyl)amide (1.17 g, 5.84 mmol) in 15 mL toluene. The reaction mixture was stirred for 90 min. at 0° C. 0.4 mL acetic acid were added, and the mixture extracted with water, saturated NaHCO3-Solution and brine. The aqueous layer was washed with toluene (100 mL). The combined organic extracts were dried with sodium sulfate and filtered. The solvent was evaporated, and the crude product [(0.8 g, 81%), [MS: m/e=424.5 (M+H+)] was used without any further purification for the next step.

Workup

  1. extractionthe mixture extracted with water, saturated NaHCO3-Solution and brine
  2. washThe aqueous layer was washed with toluene (100 mL)
  3. dry with materialThe combined organic extracts were dried with sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated
  6. customthe crude product [(0.8 g, 81%), [MS: m/e=424.5 (M+H+)] was used without any further purification for the next step

Sources & evidence

ORD record
ord-e2cbc522db054af08cf470ce3e7bb2e2
Source dataset
uspto-grants-2012_10
Patent number
US08293916B2

Reaction notes

Loading…