Potassium Carbonate → 4-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole

HRID 79461ノート

反応式

HRID 79461 の反応式
[Br: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[N:23]=[C:24]([CH3:27])[O:25][CH:26]=1>CN(C=O)C.O>[Br: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[N:23]=[C:24]([CH3:27])[O:25][CH:26]=2)[N:3]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 441196044-(Bromomethyl)-2-methyloxazoleHCID 178526560HCID 178526560、化合物

生成物 1

HCID 672615694-((3-bromo-4-nitro-1H-indazol-1-yl)methyl)-2-methyloxazole収率 43.6%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回

実験手順

A suspension of 3-bromo-4-nitro-1H-indazole (Preparation B; 500 mg, 2.07 mmol) and K2CO3 (1.14 g, 8.26 mmol) in anhydrous DMF (3 mL) was treated at ambient temperature, under a nitrogen atmosphere, with a solution of 4-(bromomethyl)-2-methyloxazole (727 mg, 2.07 mmol) (Org. Biom. Chem., 2003, 1, 4173-4208) in anhydrous DMF (2 mL). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with excess water and extracted multiple times with DCM and EtOAc. The combined extracts were dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford the crude product (0.5 g). The material was purified by preparative thin-layer chromatography (silica, 5% MeOH-DCM as eluent) to afford the product (304 mg) as a solid.

後処理

  1. extractionextracted multiple times with DCM and EtOAc
  2. dry with materialThe combined extracts were dried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto afford the crude product (0.5 g)
  5. customThe material was purified by preparative thin-layer chromatography (silica, 5% MeOH-DCM as eluent)

出典と根拠

ORDレコード
ord-fc7e86bbac614ccf843ec485b2fddcb2
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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