Sodium borohydride → HCID 68182168, compound

HRID 1620300Notes

Reaction equation

HRID 1620300 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[F:14])[N:10]=[C:9]([NH:15][CH2:16][CH3:17])[C:8]([CH:18]=[O:19])=[CH:7]2)[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][C:13]=1[F:14])[N:10]=[C:9]([NH:15][CH2:16][CH3:17])[C:8]([CH2:18][OH:19])=[CH:7]2)[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86669834HCID 86669834, compound2×

Product 1

HCID 68182168HCID 68182168, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-ethoxy-2-(ethylamino)-7-fluoroquinoline-3-carbaldehyde SMA 44102 (63 mg, 0.24 mmol) in THF (10 mL) in a 25 mL round-bottomed flask equipped with a magnetic stirrer was added NaBH4 (11 mg, 0.29 mmol) and the reaction mixture was stirred for 3 h at RT, then cooled down to 0° C. and quenched with a 6 N aq. HCl solution (5 mL). The mixture was stirred for 10 min at RT before basification to pH=12 with a 10 N aq. NaOH. THF was then removed at 40° C. and the residue was extracted with CH2Cl2 (30 mL). The organic phase was isolated, washed with brine (10 mL), dried over Na2SO4, filtered and concentrated at 40° C. under vacuum to give (6-ethoxy-2-(ethylamino)-7-fluoroquinolin-3-yl)methanol SMA 44104 as a pink solid (61 mg, 96% yield).

Workup

  1. temperaturecooled down to 0° C.
  2. customquenched with a 6 N aq. HCl solution (5 mL)
  3. stirringThe mixture was stirred for 10 min at RT before basification to pH=12 with a 10 N aq. NaOH
  4. customTHF was then removed at 40° C.
  5. extractionthe residue was extracted with CH2Cl2 (30 mL)
  6. customThe organic phase was isolated
  7. washwashed with brine (10 mL)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated at 40° C. under vacuum

Sources & evidence

ORD record
ord-fabadbee18084309a11408076ee4ded3
Source dataset
uspto-grants-2014_07
Patent number
US08772316B2

Reaction notes

Loading…