Water → HCID 67223887, compound

HRID 1259835Notes

Reaction equation

HRID 1259835 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH:12]=[O:13])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2.[BH4-].[Na+].O>CO>[F:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][OH:13])=[N:9][C:8]([O:14][CH3:15])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 86232700HCID 86232700, compound

Product 1

HCID 67223887HCID 67223887, compoundYield 79.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To an ice-chilled suspension of 3-fluoro-6-methoxy-[1.5]naphthyridine-4-carbaldehyde (5 g, 24.25 mmol; prepared as in WO 2006/032466) in MeOH (180 mL) was added NaBH4 (1.03 g, 26.68 mmol, 1.1 eq.) in one portion. After 30 min, the reaction mixture was warmed to rt. Water (180 mL) was added and the volatiles were removed under reduced pressure. The residue was filtered off and washed with water. The aq. filtrate was extracted twice with EA (2×100 mL). The combined org. layers were washed with brine (120 mL), dried over Na2SO4, filtered and evaporated under reduced pressure to afford a yellow solid. The residue was purified by CC (Hept-EA 1:1) to give the title intermediate as a pale yellow solid (4.01 g, 79% yield).

Workup

  1. customthe volatiles were removed under reduced pressure
  2. filtrationThe residue was filtered off
  3. washwashed with water
  4. extractionThe aq. filtrate was extracted twice with EA (2×100 mL)
  5. washlayers were washed with brine (120 mL)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto afford a yellow solid
  10. customThe residue was purified by CC (Hept-EA 1:1)

Sources & evidence

ORD record
ord-9d02f571dcfe4638aac0fef5e91e7a0d
Source dataset
uspto-grants-2013_06
Patent number
US08466168B2

Reaction notes

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