Sodium borohydride → HCID 86711862, compound

HRID 623776Notes

Reaction equation

HRID 623776 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[C:9]1[C:24]([N:26]([CH2:28][C:29]([C:32]#[N:33])([CH3:31])[CH3:30])[CH3:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[NH2:33][CH2:32][C:29]([CH3:31])([CH3:30])[CH2:28][N:26]([CH3:27])[C:24]([C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]([C:13]([F:16])([F:15])[F:14])=[CH:11][C:10]=1[C:17]1[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=1)=[O:25]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 86711861HCID 86711861, compound2×

Product 1

HCID 86711862HCID 86711862, compoundYield 50.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of SC-187 (31 mg, 0.276 mmol) in dry MeOH (3 mL) was added CoCl2 (54 4, 1.382 mmol) under an inert atmosphere. NaBH4 (199 mg, 5.25 mmol) was added in three equal portions under a nitrogen atmosphere at −5° C. The grey reaction mixture was stirred at room temperature during 30 min. and quenched with ice (20 mL) and aqueous 0.5 M KHSO4 (20 mL). DCM (10 mL) was added and both layers were filtered over Celite. The aqueous layer was extracted twice with DCM (10 mL). The combined organic layers were washed with brine (20 mL), dried (Na2SO4), filtered and concentrated in vacuo. Purification was performed by flash chromatography (silica, CH2Cl2/MeOH, 9:1). The appropriate fractions were combined and solvents removed in vacuo. This product was combined with the crude batch from a previous experiment performed under the same reaction conditions. In this previous experiment SC-187 (14 mg, 0.023 mmol, purity: 76%), MeOH (1 mL), CoCl2 (5.72 μL, 0.148 mmol) and NaBH4 (21.2 mg, 0.561 mmol) were used. Further purification was performed by flash chromatography (silica, DCM/MeOH/Et3N, 9:1:0.1). The appropriate fractions were combined and solvents removed in vacuo. Concentration in vacuo gave SC-188 (67 mg, 46%) as a green oil.

Workup

  1. customquenched with ice (20 mL) and aqueous 0.5 M KHSO4 (20 mL)
  2. additionDCM (10 mL) was added
  3. filtrationboth layers were filtered over Celite
  4. extractionThe aqueous layer was extracted twice with DCM (10 mL)
  5. washThe combined organic layers were washed with brine (20 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification
  10. customsolvents removed in vacuo
  11. customperformed under the same reaction conditions
  12. customFurther purification
  13. customsolvents removed in vacuo
  14. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-57181139bf39408091777a15dce62d7a
Source dataset
uspto-grants-2016_04
Patent number
US09302988B2

Reaction notes

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