Sodium borohydride → HCID 66738339, compound

HRID 1640916Notes

Reaction equation

HRID 1640916 reaction equation
[BH4-].[Na+].[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[C:16]([F:18])[N:15]=[CH:14][C:13]=3[C:19]([CH3:23])([CH3:22])[C:20]#[N:21])[C:4]1=2>C1COCC1.[Cl-].[Cl-].[Cl-].[Cl-].[Zr+4]>[S:3]1[CH:7]=[CH:6][C:5]2[CH:8]=[CH:9][CH:10]=[C:11]([C:12]3[CH:17]=[C:16]([F:18])[N:15]=[CH:14][C:13]=3[C:19]([CH3:23])([CH3:22])[CH2:20][NH2:21])[C:4]1=2

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 66738308HCID 66738308, compound

Product 1

HCID 66738339HCID 66738339, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 9856075Zirconium chloride (ZrCl4), (T-4)-CatalystHCID 8028TetrahydrofuranSolvent2×

Procedure

Dissolve sodium tetrahydroborate (296 mg, 7.83 mmol) and zirconium tetrachloride (684 mg, 2.9 mmol) in THF (1 mL) to form a milky solution. Add the solution of 2-(4-benzo[b]thiophen-7-yl-6-fluoro-pyridin-3-yl)-2-methyl-propionitrile (580 mg, 1.96 mmol) in THF (20 mL) under N2 at RT. Stir the mixture at RT overnight. Quench the reaction by pouring the mixture into an ice-water solution. Extract the mixture with chloroform/IPA (3/1). Basify the aqueous phase by adding diluted ammonium hydroxide and filter. Extract the filtrate with chloroform, dry the combined organic phase, and concentrate to give a pale yellow solid (500 mg, 84%). MS (ES) m/z 301 [M+1]+.

Workup

  1. customto form a milky solution
  2. customQuench
  3. customthe reaction
  4. extractionExtract the mixture with chloroform/IPA (3/1)
  5. additionBasify the aqueous phase by adding diluted ammonium hydroxide
  6. filtrationfilter
  7. extractionExtract the filtrate with chloroform
  8. customdry the combined organic phase
  9. concentrationconcentrate

Sources & evidence

ORD record
ord-83b5c863c92c44278d36ae25c18930dc
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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