Sodium borohydride → 7-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol

HRID 1777931Notes

Reaction equation

HRID 1777931 reaction equation
[Br:1][C:2]1[N:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1.[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[N:11]=[C:10]2[C:5]([CH:6]([OH:12])[CH2:7][CH2:8][NH:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 124403577-Bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-one

Product 1

HCID 578859587-Bromo-1,2,3,4-tetrahydro-1,8-naphthyridin-4-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 7-bromo-2,3-dihydro-1,8-naphthyridin-4(1H)-one (500 mg, 2.20 mmol) in THF (15 ml) was treated with NaBH4 (167 mg, 4.40 mmol) and stirred at 25° C. for 2 h. The reaction mixture was quenched with sat. aq. NH4Cl and extracted 2× with DCM. The org layer was dried over Na2SO4, filtered and concentrated under vacuum. The crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 50:50) to give the title compound as a white solid. (UPLC-MS 3) tR 0.59; ESI-MS 229.0, 231.0 [M+H]+.

Workup

  1. customThe reaction mixture was quenched with sat. aq. NH4Cl
  2. extractionextracted 2× with DCM
  3. dry with materialThe org layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum
  6. customThe crude material was purified by normal phase chromatography (12 g silica gel cartridge, heptanes/EtOAc 100:0 to 50:50)

Sources & evidence

ORD record
ord-aadb9818b5224e78bb338037c3905148
Source dataset
uspto-grants-2016_02
Patent number
US09266883B2

Reaction notes

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