Tributylphosphine → HCID 89690165, compound

HRID 2203005Notes

Reaction equation

HRID 2203005 reaction equation
[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1.[F:22][CH:23]([F:31])[C:24]1[S:28][C:27]([CH2:29]O)=[CH:26][CH:25]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>C1COCC1>[CH:1]1([C:4]2[N:5]=[C:6]3[CH:11]=[CH:10][C:9]([N:12]4[CH:17]=[CH:16][C:15]([O:18][CH2:29][C:27]5[S:28][C:24]([CH:23]([F:31])[F:22])=[CH:25][CH:26]=5)=[CH:14][C:13]4=[O:19])=[CH:8][N:7]3[C:20]=2[CH3:21])[CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 20079668HCID 20079668, compoundHCID 896902811-(2-Cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 89690165HCID 89690165, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1-(2-cyclopropyl-3-methylimidazo[1,2-a]pyridin-6-yl)-4-hydroxypyridin-2(1H)-one (350 mg), (5-(difluoromethyl)-2-thienyl)methanol (409 mg) and tributylphosphine (755 mg) in THF (12 ml) was added 1,1′-(azodicarbonyl)dipiperidine (942 mg), and the reaction mixture was stirred at 60° C. for 3 h. The reaction mixture was cooled to room temperature, concentrated and purified by silica gel column chromatography (hexane/EtOAc then MeOH/EtOAc). The resulting solid was recrystallized from EtOH-hexane to give the title compound (80 mg) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated
  3. custompurified by silica gel column chromatography (hexane/EtOAc
  4. customThe resulting solid was recrystallized from EtOH-hexane

Sources & evidence

ORD record
ord-2ab81e9d995c401095ba9c1e0918cf49
Source dataset
uspto-grants-2016_06
Patent number
US09365540B2

Reaction notes

Loading…