Sodium Bicarbonate → 6-(1-fluoro-2-(3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)ethyl)-3-(2-fluoro-5-methoxyphenyl)-2-neopentylpyridine

HRID 1049531Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH:21](O)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][O:30][CH:31]3[CH2:36][CH2:35][CH2:34][CH2:33][O:32]3)[CH:24]=2)=[N:14][C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].COCCN(S(F)(F)[F:48])CCOC.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[F:48][CH:21]([C:13]1[N:14]=[C:15]([CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C:10]([C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[F:1])=[CH:11][CH:12]=1)[CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][O:30][CH:31]2[CH2:36][CH2:35][CH2:34][CH2:33][O:32]2)[CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 1-(5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)-2-(3-(((tetrahydro-2H-pyran-2-yl)oxy)methyl)phenyl)ethanol (312.5 mg) in toluene (5.0 mL) was added bis(2-methoxyethyl)aminosulfur trifluoride (170 μL) at 0° C., and the mixture was stirred at 0° C. for 5 min. To the reaction mixture was added saturated aqueous sodium hydrogen carbonate solution at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give a crude product of the title compound as an orange oil. This compound was used for the next step without further purification.

Workup

extractionthe mixture was extracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-0187bc46119c4f8f88a29e40b91bbe22
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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