4-Bromo-2-hydroxypyridine → HCID 86728092, compound

HRID 2202654Notes

Reaction equation

HRID 2202654 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[O:9]1[CH2:11][C@H:10]1[CH2:12][N:13]1[CH2:22][CH2:21][C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14]1>CCO>[Br:1][C:2]1[CH:7]=[CH:6][N:5]([CH2:11][C@H:10]([OH:9])[CH2:12][N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[CH2:14]2)[C:4](=[O:8])[CH:3]=1

Participants

4

Reactant 2

HCID 8171154-Bromo-2-hydroxypyridineHCID 30076569(R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 86728092HCID 86728092, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of 4-bromopyridin-2(1H)-one (1 g, 5.747 mmol) in EtOH (3 mL) was added (R)-2-(oxiran-2-ylmethyl)-1,2,3,4-tetrahydroisoquinoline (1.087 g, 5.747 mmol). The mixture was heated under microwave conditions at 120° C. for 0.5 h and concentrated. The crude product was purified by column chromatography eluting with DCM/MeOH (10:1). (475 mg, yield 22.8%) MS (ESI+) e/z: 363.1 [M+1]+.

Workup

  1. concentrationconcentrated
  2. customThe crude product was purified by column chromatography
  3. washeluting with DCM/MeOH (10:1)

Sources & evidence

ORD record
ord-9f73a23e986443e19cc79ee6817c8782
Source dataset
uspto-grants-2016_06
Patent number
US09365555B2

Reaction notes

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