Tetrahydrofuran → HCID 67073731, compound

HRID 2103426Notes

Reaction equation

[H-].[Na+].[CH3:3][C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9][OH:10].[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:29]=[CH:28][C:27](CBr)=[CH:26][CH:25]=1.[CH2:33]1COCC1>C(OCC)(=O)C>[CH3:21][O:22][C:23](=[O:32])[C:24]1[CH:25]=[CH:26][C:27]([CH:9]([C:8]2[S:7][C:6]([C:11]3[CH:12]=[CH:13][C:14]([C:17]([F:20])([F:18])[F:19])=[CH:15][CH:16]=3)=[N:5][C:4]=2[CH3:3])[O:10][CH3:33])=[CH:28][CH:29]=1

Participants

Conditions

Temperature: -5 °C

Procedure

Cool (−5° C.) a suspension of NaH (84 mg, 60% dispersion in mineral oil, 2.05 mmol) in THF (4 mL) and add a solution comprised of 2-([4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl)-methanol (546 mg, 2 mmol) and 4-bromomethyl-benzoic acid methyl ester (458 mg, 2 mmol) in THF (5 mL). Stir the resulting mixture for 5 min then the remove the cold bath and stir for an additional 3 hr. Quench the reaction with 1M HCl solution, dilute with ethyl acetate, wash with brine and dry over Mg SO4. Concentrate this solution under vacuum and purify the residue by flash chromatography (eluting with 20% ethyl acetate in heptane) to give the product (377 mg) as a white solid.

Workup

additionadd a solution
customthe remove the cold bath
stirringstir for an additional 3 hr
customQuench
customthe reaction with 1M HCl solution
washwash with brine
dry with materialdry over Mg SO4
concentrationConcentrate this solution under vacuum
custompurify the residue
washby flash chromatography (eluting with 20% ethyl acetate in heptane)

Sources & evidence

ORD record: ord-b0d39b60b5a1490dabf0c9640e12fc7f
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07576109B2

Reaction notes

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