Sodium borohydride → HCID 67305210, compound

HRID 2280258Notes

Reaction equation

HRID 2280258 reaction equation
[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]=[O:12].[BH4-].[Na+]>C(O)C>[N:1]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 115863361,5-Naphthyridine-2-carbaldehyde

Product 1

HCID 67305210HCID 67305210, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 mL round bottom flask equipped with a magnetic stirbar was charged with Intermediate 4B, 1,5-naphthyridine-2-carbaldehyde (200 mg, 1.265 mmol). Ethanol (12.6 mL) was added to give a solution. To this stirred solution was added, portionwise, sodium borohydride (47.8 mg, 1.265 mmol). The reaction mixture was stirred at ambient temperature for 15 minutes, then quenched with aqueous sodium bicarbonate. Volatiles were removed under reduced pressure and the residue was partitioned between EtOAc and water. The aqueous layer was extracted once more with EtOAc, then the combined organic layers were dried (MgSO4) and filtered. The filtrate was concentrated under reduced pressure to give (1,5-naphthyridin-2-yl)methanol as a pale yellow solid that was purified by eluting through a plug of silica gel with 100% EtOAc. After evaporation of the solvent under reduced pressure, an off white solid was obtained, which was dried in a vacuum oven at ambient temperature for 3 days to give (1,5-naphthyridin-2-yl)methanol (142 mg, 70%). 1H NMR (300 MHz, methanol-d4) δ 8.94 (dd, J=4.3, 1.6 Hz, 1H), 8.47-8.40 (m, 2H), 7.96 (d, J=8.8 Hz, 1H), 7.79 (dd, J=8.6, 4.3 Hz, 1H), 4.91 (s, 2H). MS (DCI—NH3) m/z=161 (M+H)+, m/z=178 (M+NH4)+.

Workup

  1. customA 100 mL round bottom flask equipped with a magnetic stirbar
  2. customto give a solution
  3. additionTo this stirred solution was added
  4. customquenched with aqueous sodium bicarbonate
  5. customVolatiles were removed under reduced pressure
  6. customthe residue was partitioned between EtOAc and water
  7. extractionThe aqueous layer was extracted once more with EtOAc
  8. dry with materialthe combined organic layers were dried (MgSO4)
  9. filtrationfiltered
  10. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-78a75a8c564544ea96caef355387a0b0
Source dataset
uspto-grants-2015_09
Patent number
US09138494B2

Reaction notes

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