4-Methoxypyridine → HCID 86598850, compound

HRID 1992445Notes

Reaction equation

Cl[C:2]([O:4][CH:5]1[CH:10]([CH:11]([CH3:13])[CH3:12])[CH2:9][CH2:8][CH:7]([CH3:14])[CH2:6]1)=[O:3].C[O:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=1.[F:23][C:24]1[CH:29]=[CH:28][C:27]([Mg]Br)=[C:26]([CH3:32])[CH:25]=1>C1COCC1>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C@H:21]2[CH2:22][C:17](=[O:16])[CH:18]=[CH:19][N:20]2[C:2]([O:4][C@@H:5]2[CH2:6][C@H:7]([CH3:14])[CH2:8][CH2:9][C@H:10]2[CH:11]([CH3:13])[CH3:12])=[O:3])=[C:26]([CH3:32])[CH:25]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of (−)-menthyl chloroformate (3.53 mL) in dry THF (15 mL) was added to a solution of 4-methoxypyridine (1.52 mL) in dry THF (35 mL) previously cooled to −78° C. under a nitrogen atmosphere. After 15 minutes, the solution containing the 4-fluoro-2-methyl-phenyl magnesium bromide was added drop-wise, and the mixture was stirred at −78° C. for 1 hour. The reaction was quenched by the addition of 1M hydrochloric acid solution (20 mL), warmed to r.t. and stirred at 23° C. for 30 minutes. After extraction with AcOEt (2×150 mL), the combined organic extracts were washed with brine (50 mL), dried and concentrated in vacuo to a residue, which was purified by flash chromatography (CH/THF/toluene 8:1:1) to give:

Workup

additionwas added drop-wise
customThe reaction was quenched by the addition of 1M hydrochloric acid solution (20 mL)
temperaturewarmed to r.t.
stirringstirred at 23° C. for 30 minutes
extractionAfter extraction with AcOEt (2×150 mL)
washthe combined organic extracts were washed with brine (50 mL)
customdried
concentrationconcentrated in vacuo to a residue, which
customwas purified by flash chromatography (CH/THF/toluene 8:1:1)
customto give

Sources & evidence

ORD record: ord-7d51999170544d5a8c123aaccf71f621
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07648990B2

Reaction notes

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