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

HRID 2193705ノート

反応式

HRID 2193705 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24385Nickel Dichloride触媒HCID 21899815MeOH tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-be1a12626222400e999cf647e3d2c42f
出典データセット
uspto-grants-2012_12
特許番号
US08329726B2

反応ノート

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