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

HRID 2193709Notes

Reaction equation

HRID 2193709 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]([CH2:19][CH2:20][CH3:21])[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]([CH2:19][CH2:20][CH3:21])[CH:18]=3)[S:13][C:6]=12)[NH2:26]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 587903777-(2-Fluoro-4-nitrophenoxy)-2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridine

Product 1

HCID 587904093-Fluoro-4-(2-(1-propyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)anilineYield 86.7%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the nitro compound 132 (4.13 g, 10.36 mmol) in MeOH/THF (100 ml/100 mL) was added NiCl2×6H2O (4.92 g, 20.73 mmol) and NaBH4 (1.54 mg, 41.44 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) to afford title compound 133 (3.31 g, 86% yield) as a pink solid. MS (m/z): 368.1 (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 The residue
  8. customwas purified by flash chromatography (eluents DCM-MeOH, 98:2, 95:5)

Sources & evidence

ORD record
ord-cd658a10a8664650bc33fe7c1ccd5ef8
Source dataset
uspto-grants-2012_12
Patent number
US08329726B2

Reaction notes

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