Potassium Carbonate → 5-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole

HRID 706740노트

반응식

HRID 706740 반응식
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:21][C:22]1[S:26][C:25]([CH3:27])=[N:24][CH:23]=1>CN(C=O)C.O.CCOC(C)=O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:21][C:22]2[S:26][C:25]([CH3:27])=[N:24][CH:23]=2)[N:3]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 552507865-(Bromomethyl)-2-methyl-1,3-thiazoleHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 679761065-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole수율 99.8%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of 3-iodo-4-nitro-1H-indazole (441 mg, 1.53 mmol) in anhydrous DMF (3 mL) were added potassium carbonate (422 mg, 3.05 mmol), and 5-(bromomethyl)-2-methylthiazole (440 mg, 2.30 mmol) at ambient temperature and under a nitrogen atmosphere. The resulting mixture was stirred at ambient temperature overnight (about 18 hours). The reaction mixture was diluted with water (10 mL) and EtOAc (20 mL). The phases were separated and the aqueous phase was extracted with EtOAc (2×25 mL). The combined organic extracts were concentrated, and the residue subjected to flash liquid chromatography on silica with Hexanes:EtOAc (10:1) as the eluent to afford the desired product (611 mg).

후처리

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×25 mL)
  3. concentrationThe combined organic extracts were concentrated

출처 및 근거

ORD 기록
ord-580bce65506544febaeb4232d83d5177
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09174981B2

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