3-Pentanol → HCID 22249119, compound

HRID 889877Notes

Reaction equation

[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Br[C:10]1[N:11]=[C:12]([O:31][CH3:32])[C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:20][C:19]=2[O:29][CH3:30])=[N:14][C:15]=1[CH2:16][CH3:17]>C1COCC1>[CH2:16]([C:15]1[N:14]=[C:13]([C:18]2[CH:28]=[CH:27][C:21]([O:22][C:23]([F:26])([F:25])[F:24])=[CH:20][C:19]=2[O:29][CH3:30])[C:12]([O:31][CH3:32])=[N:11][C:10]=1[O:6][CH:3]([CH2:4][CH3:5])[CH2:2][CH3:1])[CH3:17]

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred solution of 3-pentanol (88 mg, 1 mmol) in THF (1 mL) is added 60% sodium hydride (12 mg, 0.3 mmol) and after 0.5 h [4-(5-bromo-6-ethyl-3-methoxypyrazin-2-yl)-3-methoxyphenoxy]trifluoromethane (41 mg, 0.1 mmol) is added. The mixture is heated to 50° C. for 12 h, cooled and partitioned between ethyl acetate and water. The organic layer is washed with water, brine, dried (sodium sulfate), filtered and concentrated. The residue is purified by preparative TLC eluting with 50% ether in hexanes to give {4-[6-Ethyl-5-(ethylpropoxy)-3-methoxypyrazin-2-yl]-3-methoxyphenoxy}trifluoromethane, a colorless oil (19 mg). NMR (CDCL3, 400 MHz) □0.98 (t, 6 H), 1.22 (t, 3 H), 1.78 (m, 4 H) 2.80 (q, 2 H), 3.80 (s, 3 H), 3.88 (s, 3 H), 5.05 (quintet, 1 H), 6.8 (s, 1 H), 6.90 (d, 1 H), 7.37 (d, 1 H); MS 345 (M+1).

Workup

temperaturecooled
custompartitioned between ethyl acetate and water
washThe organic layer is washed with water, brine
dry with materialdried (sodium sulfate)
filtrationfiltered
concentrationconcentrated
customThe residue is purified by preparative TLC
washeluting with 50% ether in hexanes

Sources & evidence

ORD record: ord-81b5035f9c3c4183b65a9ea659ccf76c
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06995161B2

Reaction notes

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