Sodium borohydride → (7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

HRID 418582

Reaction equation

HRID 418582 reaction equation
[F:1][C:2]1[CH:24]=[C:23]([N+:25]([O-])=O)[CH:22]=[CH:21][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]([N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:15])[S:13][C:6]=12.[BH4-].[Na+]>CO.C1COCC1>[NH2:25][C:23]1[CH:22]=[CH:21][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]([N:16]4[CH2:17][CH2:18][CH2:19][CH2:20]4)=[O:15])[S:13][C:6]=23)=[C:2]([F:1])[CH:24]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59424552(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanone

Product 1

HCID 59424653(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(pyrrolidin-1-yl)methanoneYield 91.4%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 22 (3.23 g, 8.33 mmol) and NiCl2.6H2O (3.96 g, 16.66 mmol) in MeOH/THF (100/100 mL) was added NaBH4 (1.24 g, 33.32 mmol). The reaction mixture was stirred for 1 hr, concentrated to dryness and the resultant solid was dissolved in 10% HCl. The aqueous solution was then made basic with concentrated NH4OH solution and extracted with EtOAc. The organic phase was collected, dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford 23 as a black solid (2.72 g, 91% yield). MS (m/z): 358.2 (M+H).

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionthe resultant solid was dissolved in 10% HCl
  3. extractionextracted with EtOAc
  4. customThe organic phase was collected
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c41c3a060d654400a4e9cd6ff5b771ad
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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