Ammonium Hydroxide → 3-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

HRID 418579Notes

Reaction equation

HRID 418579 reaction equation
[F:1][C:2]1[CH:23]=[C:22]([N+:24]([O-])=O)[CH:21]=[CH:20][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:18]([CH3:19])[CH:17]=[N:16][CH:15]=3)[S:13][C:6]=12.[BH4-].[Na+].[NH4+].[OH-]>CO.C1COCC1.Cl>[F:1][C:2]1[CH:23]=[C:22]([NH2:24])[CH:21]=[CH:20][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:18]([CH3:19])[CH:17]=[N:16][CH:15]=3)[S:13][C:6]=12

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 4311764Sodium borohydrideHCID 666494047-(2-Fluoro-4-nitrophenoxy)-2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridine

Product 1

HCID 594244313-Fluoro-4-(2-(1-methyl-1H-imidazol-5-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamineYield 52.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a stirring mixture of the nitro compound 17 (0.96 g, 2.59 mmol) and NiCl2.6H2O (1.24 g, 5.22 mmol) in MeOH/THF (26 mL/39 mL) at 0° C., NaBH4 (0.341 g, 9.01 mmol) was added portion wise. The reaction mixture was stirred for 15 minutes, quenched with 1M HCl (10 mL) and concentrated under reduced pressure to form a green residue, which was then dissolved in 1M HCl (250 mL) and basified with NH4OH. The cloudy suspension was extracted with EtOAc, the organic layer was collected, filtered, washed with water and then dried over anhydrous Na2SO4. Evaporation of this solution afforded title compound 18 as brown solid (0.46 g, 52% yield), which was used in the next step without additional purification. MS (m/z): 341.1 (M+H).

Workup

  1. customquenched with 1M HCl (10 mL)
  2. concentrationconcentrated under reduced pressure
  3. customto form a green residue, which
  4. extractionThe cloudy suspension was extracted with EtOAc
  5. customthe organic layer was collected
  6. filtrationfiltered
  7. washwashed with water
  8. dry with materialdried over anhydrous Na2SO4
  9. customEvaporation of this solution

Sources & evidence

ORD record
ord-16bf3b5526ee488ab8b8c4da980f3aad
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Reaction notes

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