Sodium borohydride → HCID 68089094, compound

HRID 2370258Notes

Reaction equation

HRID 2370258 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:19][CH2:18][C:17]3[N:16]=[CH:15][C:14]([CH:20]=C)=[CH:13][C:12]=3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1.[BH4-].[Na+].C(Cl)Cl.C[OH:28]>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:10]2[CH2:19][CH2:18][C:17]3[N:16]=[CH:15][C:14]([CH2:20][OH:28])=[CH:13][C:12]=3[CH2:11]2)=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 21226129Dichloromethane methanolHCID 68089334HCID 68089334, compound

Product 1

HCID 68089094HCID 68089094, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(4-Fluorophenyl)(3-vinyl-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone (50 mg, 0.2 mmol; prepared as described above) was dissolved in CH2Cl2:MeOH (9:1, 15 mL) and cooled in a dry ice/acetone bath. Ozone was bubbled through the solution for 3 min and the reaction was allowed to warm to RT as then purged with an air inlet for 5 min. Sodium borohydride (65 mg, 1.7 mmol) in MeOH (10 mL) was added and the reaction allowed to stir for 1 h. The reaction mixture was concentrated, partitioned between water and EtOAc, and the water layer extracted with CH2Cl2:butanol (9:1). The volatiles were removed under reduced pressure to give 40 mg of crude product. The crude (4-fluorophenyl)(3-(hydroxymethyl)-7,8-dihydro-1,6-naphthyridin-6(5H)-yl)methanone was used in the next step without further purification. LC-MS (M+H)=287.2.

Workup

  1. temperaturecooled in a dry ice/acetone bath
  2. customOzone was bubbled through the solution for 3 min
  3. customas then purged with an air inlet for 5 min
  4. concentrationThe reaction mixture was concentrated
  5. custompartitioned between water and EtOAc
  6. extractionthe water layer extracted with CH2Cl2:butanol (9:1)
  7. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-718d038337ed4b329551455e8aa6536a
Source dataset
uspto-grants-2014_04
Patent number
US08710074B2

Reaction notes

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