HCID 86672835, compound → HCID 86672834, compound

HRID 1423036Notes

Reaction equation

HRID 1423036 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([CH:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[NH:9][CH:10]=O)[CH:5]=[CH:4][CH:3]=1>O=P(Cl)(Cl)Cl>[Br:1][C:2]1[N:7]2[CH:10]=[N:9][C:8]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)=[C:6]2[CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 86672835HCID 86672835, compound

Product 1

HCID 86672834HCID 86672834, compound

Reagents, catalysts & solvents 1

HCID 24813Phosphorus oxychlorideSolvent

Procedure

A stirred mixture of N-[(6-bromopyridin-2-yl)-(4-fluorophenyl)-methyl]-formamide (6.4 g, 21 mmol) in POCl3 (41 mL) is warmed at reflux. After 1 hour, the reaction mixture is cautiously quenched by a slow addition to saturated aqueous NaHCO3 and the mixture is extracted into EtOAc (3×200 mL). The combined organic layers are dried over Na2SO4 and concentrated. The crude material is purified by silica gel chromatography eluting with 30% EtOAc in hexanes to afford 5-bromo-1-(4-fluorophenyl)-imidazo[1,5-a]pyridine.

Workup

  1. temperatureis warmed
  2. temperatureat reflux
  3. customthe reaction mixture is cautiously quenched by a slow addition to saturated aqueous NaHCO3
  4. extractionthe mixture is extracted into EtOAc (3×200 mL)
  5. dry with materialThe combined organic layers are dried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude material is purified by silica gel chromatography
  8. washeluting with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-08d17ed8f74549a28ea3477becbf057a
Source dataset
uspto-grants-2015_01
Patent number
US08927550B2

Reaction notes

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