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

HRID 418640Notes

Reaction equation

HRID 418640 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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).

Workup

  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)

Sources & evidence

ORD record
ord-66fea113357d4906bd71562386fa0772
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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