Sodium Methoxide → 2-Methoxy-3-(1-ethylpropoxy)-6-(2-methoxy-4-trifluoromethoxyphenyl)-5-methylpyridine

HRID 1354238Notes

Reaction equation

[CH3:1][O-:2].[Na+].Cl[C:5]1[C:10]([O:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:9][C:8]([CH3:17])=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=2[O:29][CH3:30])[N:6]=1>CO.CN1C(=O)CCC1.CCOC(C)=O.CCCCCC>[CH3:1][O:2][C:5]1[C:10]([O:11][CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])=[CH:9][C:8]([CH3:17])=[C:7]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:20][C:19]=2[O:29][CH3:30])[N:6]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Sodium methoxide in methanol (25 w/w %, 0.5 ml) is added to a solution of compound 45 (50 mg, 0.124 mmol) in NMP (0.5 ml). The resulting mixture is heated to 100° C. overnight, then cooled to room temperature, diluted with 50% EtOAc in hexane, washed with water, brine, dried, filtered and evaporated. The crude product is purified by chromatography (eluted with 6% EtOAc in hexane) to give the product as colorless oil. 1H NMR (CDCl3) δ 1.00 (t, J=7.6 Hz, 6H), 1.75 (m, 4H), 2.04 (s, 3H), 3.80 (s, 3H), 3.94 (s, 3H), 4.12 (m. 1H), 6.78 (s, 1H), 6.89 (dd, 1H), 6.92 (s, 1H), 7.30 (d, J=8.4 Hz, 1H). LCMS 400.4 (M+1).

Workup

temperaturecooled to room temperature
washwashed with water, brine
customdried
filtrationfiltered
customevaporated
customThe crude product is purified by chromatography (eluted with 6% EtOAc in hexane)

Sources & evidence

ORD record: ord-589aea7953ec40e3a23b3bb03437f7b0
Source dataset: uspto-grants-2007_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07223778B2

Reaction notes

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