Sodium borohydride → 4-(2-(4-Methyl-1H-pyrazol-1-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamine

HRID 1711029Notes

Reaction equation

HRID 1711029 reaction equation
[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[O:16][C:17]3[CH:22]=[CH:21][C:20]([N+:23]([O-])=O)=[CH:19][CH:18]=3)[CH:8]=2)[CH:6]=1.[BH4-].[Na+]>CO.C1COCC1.Cl[Ni]Cl>[CH3:1][C:2]1[CH:3]=[N:4][N:5]([C:7]2[S:15][C:14]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[O:16][C:17]3[CH:22]=[CH:21][C:20]([NH2:23])=[CH:19][CH:18]=3)[CH:8]=2)[CH:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 594244922-(4-Methyl-1H-pyrazol-1-yl)-7-(4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 686921064-(2-(4-Methyl-1H-pyrazol-1-yl)thieno[3,2-b]pyridin-7-yloxy)benzenamineYield 87.3%

Reagents, catalysts & solvents 2

HCID 24385Nickel DichlorideCatalystHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 256 (168.4 mg, 0.478 mmol) and NiCl2×6H2O (226 mg, 0.956 mmol) in MeOH/THF (10/10 mL) NaBH4 (72 mg, 1.92 mmol) was carefully added. The reaction mixture was stirred for 10 min, concentrated to dryness and the resultant solid was suspended in 10% HCl. The aqueous solution was basified (pH ˜11) with concentrated aqueous NH4OH and extracted with EtOAc. The organic extract was collected, dried over anhydrous Na2SO4 and concentrated under reduced pressure, to afford title compound 257 (134.6 mg, 87% yield) as a white solid. MS (m/z): 322.09 (M+1).

Workup

  1. concentrationconcentrated to dryness
  2. extractionextracted with EtOAc
  3. extractionThe organic extract
  4. customwas collected
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2232855a4486400383432d0a3153db46
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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