Triphenylphosphine → Methyl 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylate

HRID 1251922Notes

Reaction equation

HRID 1251922 reaction equation
CCOC(/N=N/C(OCC)=O)=O.[F:13][C:14]1[CH:32]=[CH:31][C:17]([CH2:18][CH2:19][C:20]2[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([OH:26])=[CH:24][CH:25]=2)=[CH:16][CH:15]=1.[CH3:33][N:34]1[C:38]([CH2:39][CH:40]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=2)O)=[CH:37][N:36]=[CH:35]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:18][CH2:19][C:20]2[C:21]([C:27]([O:29][CH3:30])=[O:28])=[N:22][C:23]([O:26][CH:40]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=3)[CH2:39][C:38]3[N:34]([CH3:33])[CH:35]=[N:36][CH:37]=3)=[CH:24][CH:25]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 183244771-(4-Fluorophenyl)-2-(1-methylimidazol-5-yl)ethanolHCID 178499128Methyl 3-(4-fluorophenethyl)-6-hydroxypyridin-2-carboxylate

Product 1

HCID 18324461Methyl 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylateYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

DEAD (0.85 ml) was added dropwise over 2 minutes to a stirred suspension of methyl 3-(4-fluorophenethyl)-6-hydroxypyridin-2-carboxylate (1.0 g), 2-(1-methylimidazol-5-yl)-1-(4-fluorophenyl)ethanol (0.80 g) and triphenylphosphine (1.43 g) in THF (70 ml) under an inert atmosphere at ambient temperature. After stirring for 16 hours the solution was concentrated under reduced pressure and loaded directly onto a silica flash column eluting with methanol/dichloromethane (1:20) to give methyl 3-(4-fluorophenethyl)-6-[1-(4-fluorophenyl)-2-(1-methylimidazol-5-yl)ethoxy]pyridin-2-carboxylate as a colourless oil (1.56 g).

Workup

  1. concentrationwas concentrated under reduced pressure
  2. washeluting with methanol/dichloromethane (1:20)

Sources & evidence

ORD record
ord-bf856a5a5c614d139e84300b22756159
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

Loading…