Dichloromethane → 4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole

HRID 79471ノート

反応式

HRID 79471 の反応式
I[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]([CH2:14][C:15]2[S:16][CH:17]=[C:18]([CH3:20])[N:19]=2)[N:3]=1.[CH2:21](N(CC)CC)[CH3:22].[B-](F)(F)(F)C=C.[K+].ClCCl>CC(O)C.C1COCC1>[CH3:20][C:18]1[N:19]=[C:15]([CH2:14][N:4]2[C:5]3[C:10](=[C:9]([N+:11]([O-:13])=[O:12])[CH:8]=[CH:7][CH:6]=3)[C:2]([CH:21]=[CH2:22])=[N:3]2)[S:16][CH:17]=1

参加物

6

反応物 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 23679353Potassium vinyltrifluoroborateHCID 672597432-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole

生成物 1

HCID 672609244-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole収率 80.5%

試薬・触媒・溶媒 1

HCID 22597222Tetrahydrofuran 2-propanol溶媒

反応条件

温度
90 °C

実験手順

A suspension of 2-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-4-methylthiazole (0.414 g, 1.03 mmol) in IPA/THF (4:1; 15 mL) was degassed with argon, treated with triethylamine (0.433 mL, 3.10 mmol), potassium trifluoro(vinyl)borate (0.416 g, 3.10 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (0.0845 g, 0.103 mmol). The mixture was heated at 90° C. for 14 hours under argon. The mixture was filtered through glass fiber filter paper, concentrated under reduced pressure and purified by silica gel chromatography (10-75% EtOAc in hexanes) to provide 4-methyl-2-((4-nitro-3-vinyl-1H-indazol-1-yl)methyl)thiazole (0.249 g, 80% yield) as an amber gum.

後処理

  1. customwas degassed with argon
  2. filtrationThe mixture was filtered through glass fiber
  3. filtrationfilter paper
  4. concentrationconcentrated under reduced pressure
  5. custompurified by silica gel chromatography (10-75% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-a31ab11f0afc4773a5372ba13f582d0a
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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