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

HRID 706740ノート

反応式

HRID 706740 の反応式
[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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-580bce65506544febaeb4232d83d5177
出典データセット
uspto-grants-2015_11
特許番号
US09174981B2

反応ノート

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