Sodium borohydride → HCID 58873178, compound

HRID 1990096Notes

Reaction equation

HRID 1990096 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[S:9][C:10](S(C)(=O)=O)=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:15][CH:14]=1)=[O:7])[CH3:4]>CCO>[CH2:3]([O:5][C:6]([C:8]1[S:9][CH:10]=[C:11]([C:27]#[N:28])[C:12]=1[C:13]1[CH:14]=[CH:15][C:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]#[N:26])=[CH:17][CH:18]=1)=[O:7])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58873081HCID 58873081, compound

Product 1

HCID 58873178HCID 58873178, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Add NaBH4 (10 mg, 0.26 mmol) to a solution of 4-cyano-3-(2′-cyano-biphenyl-4-yl)-5-methanesulfonyl-thiophene-2-carboxylic acid ethyl ester (95 mg, 0.22 mmol) in 2 mL of EtOH at 0° C. Remove the ice-bath and stir at room temperature. After 30 minutes add another 10 mg of NaBH4 and stir an additional 30 minutes. Remove the solvents in vacuo and extract the residue with 50 mL of 1/9 MeOHJ CH2Cl2. Evaporate and chromatograph over silica gel (100/0 to 90/10 toluene/EtOAc) to give 44 mg (56%) of the title compound as a white solid. HPLC=94%.

Workup

  1. customRemove the ice-bath
  2. additionAfter 30 minutes add another 10 mg of NaBH4
  3. stirringstir an additional 30 minutes
  4. customRemove the solvents in vacuo
  5. extractionextract the residue with 50 mL of 1/9 MeOHJ CH2Cl2
  6. customEvaporate

Sources & evidence

ORD record
ord-32b79f51225745f3b6cd6b79ae703088
Source dataset
uspto-grants-2010_01
Patent number
US07642361B2

Reaction notes

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