Sodium borohydride → 3-Fluoro-4-(2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 418640노트

반응식

HRID 418640 반응식
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH:19]([CH3:21])[CH3:20])[CH:18]=3)[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1.Cl[Ni]Cl>[F:1][C:2]1[CH:25]=[C:24]([CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH:19]([CH3:21])[CH3:20])[CH:18]=3)[S:13][C:6]=12)[NH2:26]

참가 물질

5

반응물 2

HCID 4311764Sodium borohydrideHCID 587903897-(2-Fluoro-4-nitrophenoxy)-2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

생성물 1

HCID 587903973-Fluoro-4-(2-(1-isopropyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline수율 244.1%

시약·촉매·용매 2

HCID 24385Nickel Dichloride촉매HCID 21899815MeOH tetrahydrofuran용매

실험 절차

To a solution of the nitro compound 124 (1.47 g, 3.68 mmol) in MeOH/THF (50 ml/50 mL) was added NiCl2×6H2O (1.75 g, 7.37 mmol) and NaBH4 (550 mg, 14.75 mmol). The reaction mixture was allowed to stir for 1 hr then concentrated to dryness and the resultant solid was dissolved in 2 M HCl. The acidic solution was then made basic with aqueous ammonium hydroxide solution and extracted with EtOAc. The organic extract was dried over anhydrous sodium sulfate, filtered and evaporated The residue was purified by flash chromatography (eluents DCM-MeOH, 98:2, 95:5, 9:1) to afford title compound 125 (3.31 g, 88% yield) as a pink solid. MS (m/z): 368.1 (M+H).

후처리

  1. concentrationthen concentrated to dryness
  2. dissolutionthe resultant solid was dissolved in 2 M HCl
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customevaporated The residue
  8. customwas purified by flash chromatography (eluents DCM-MeOH, 98:2, 95:5, 9:1)

출처 및 근거

ORD 기록
ord-66fea113357d4906bd71562386fa0772
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093264B2

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