Sodium borohydride → HCID 68182206, compound

HRID 1620271Notes

Reaction equation

HRID 1620271 reaction equation
[CH2:1]([NH:3][C:4]1[C:13]([CH:14]=[O:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([F:18])=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([NH:3][C:4]1[C:13]([CH2:14][OH:15])=[CH:12][C:11]2[C:6](=[CH:7][C:8]([F:18])=[C:9]([O:16][CH3:17])[CH:10]=2)[N:5]=1)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86669831HCID 86669831, compound2×

Product 1

HCID 68182206HCID 68182206, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(ethylamino)-7-fluoro-6-methoxyquinoline-3-carbaldehyde CCH 42068 (500 mg, 2.01 mmol) in THF (50 mL) in a 100 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (80 mg, 2.11 mmol) and the reaction mixture was stirred overnight at RT, then cooled in an ice bath and quenched by addition of a 6 N aqueous HCl solution (10 mL). The mixture was then basified with a 10 N aqueous NaOH solution (to pH=12). THF was then removed at 40° C. under vacuum and the residue was taken up in CH2Cl2 (50 mL) and the organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum. Purification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50) followed by a new purification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 90:10) gave (2-ethylamino-7-fluoro-6-methoxyquinolin-3-yl)methanol SMA 44090 as a white solid (290 mg, 58% yield).

Workup

  1. temperaturecooled in an ice bath
  2. customquenched by addition of a 6 N aqueous HCl solution (10 mL)
  3. customTHF was then removed at 40° C. under vacuum
  4. customthe organic phase was isolated
  5. washwashed with brine (10 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated at 40° C. under vacuum
  9. customPurification by column chromatography (SiO2, eluent cyclohexane:EtOAc=100:0 to 50:50)
  10. customfollowed by a new purification by column chromatography (SiO2, eluent CH2Cl2:EtOAc=100:0 to 90:10)

Sources & evidence

ORD record
ord-6d23940017bd4cd39259989fc324d098
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

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