Sodium borohydride → 4-(2-(1-Ethyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroaniline

HRID 418637Notes

Reaction equation

HRID 418637 reaction equation
[CH2:1]([N:3]1[C:7]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][C:19]=3[F:27])[CH:9]=2)=[CH:6][N:5]=[CH:4]1)[CH3:2].[BH4-].[Na+]>CO.C1COCC1.Cl[Ni]Cl>[CH2:1]([N:3]1[C:7]([C:8]2[S:16][C:15]3[C:10](=[N:11][CH:12]=[CH:13][C:14]=3[O:17][C:18]3[CH:23]=[CH:22][C:21]([NH2:24])=[CH:20][C:19]=3[F:27])[CH:9]=2)=[CH:6][N:5]=[CH:4]1)[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 587900622-(1-Ethyl-1H-imidazol-5-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 587904254-(2-(1-Ethyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)-3-fluoroanilineYield 71.2%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the nitro compound 119 (3.05 g, 7.93 mmol) in MeOH/THF (50 ml/50 mL) was added NiCl2×6H2O (3.77 g, 15.86 mmol) and NaBH4 (1.18 g, 31.73 mmol). The reaction mixture was allowed to stir for 1 hr, 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 120 (2.00 g, 71% yield) as a yellow solid. MS (m/z): 355.1 (M+H).

Workup

  1. concentrationconcentrated 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
  8. customThe residue was purified by flash chromatography (eluents DCM-MeOH, 98:2, 95:5, 9:1)

Sources & evidence

ORD record
ord-0876f5c815db4580b05ecb05cdb59636
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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