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

HRID 79471노트

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HRID 79471 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 22597222Tetrahydrofuran 2-propanol용매

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온도
90 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-a31ab11f0afc4773a5372ba13f582d0a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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