Water → HCID 67059764, compound

HRID 1671291Notes

Reaction equation

HRID 1671291 reaction equation
[H-].[Na+].[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([F:21])([F:20])[F:19])=[CH:15][CH:16]=3)[NH:11][N:10]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:23][C:24]1[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=1.O>CN(C)C=O>[C:3]1([C:9]2[C:17]3[C:12](=[CH:13][C:14]([C:18]([F:20])([F:21])[F:19])=[CH:15][CH:16]=3)[N:11]([CH2:23][C:24]3[S:25][CH:26]=[C:27]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:28]=3)[N:10]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 11043146Ethyl 2-(bromomethyl)-1,3-thiazole-4-carboxylateHCID 67059763HCID 67059763, compound

Product 1

HCID 67059764HCID 67059764, compoundYield 10.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (added with 40% mineral oil, 20 mg, manufacture by Kanto Chemical Co., Inc.) was added to a solution of 3-phenyl-6-(trifluoromethyl)-1H-indazole (40 mg), which had been synthesized in Reference Example 18 according to the methods of Reference Examples 8 and 9, in N,N-dimethylformamide (1 mL, manufactured by Kanto Chemical Co., Inc.) under ice cooling, and the mixture was stirred for 5 minutes at the same temperature. Subsequently, ethyl 2-bromomethylthiazole-4-carboxylate (114 mg) synthesized according to the method of the literature (K. Benno, et al., Liebigs. Ann. Chem., 1981, 4, 623-632) was added thereto, and the mixture was stirred overnight at room temperature. Water (1 mL) was added to the reaction solution, and the mixture was extracted with ethyl acetate (3×2 mL), washed with brine (10 mL), and dried (MgSO4). The solvent was then evaporated. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1), to give 7.2 mg of the title compound. LC-MS: HPLC retention time 1.41 minutes, m/z 404 (M+H), condition C-1.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate (3×2 mL)
  4. washwashed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. customThe solvent was then evaporated
  7. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-3056fa485c60430d9589c8c20caaec21
Source dataset
uspto-grants-2011_08
Patent number
US07994202B2

Reaction notes

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