3,4-dihydro-2H-pyran → 2-Bromo-6-(tetrahydro-pyran-2-yloxymethyl)-4-(4-trifluoromethyl-phenyl)-pyridine

HRID 1989131Notes

Reaction equation

[Br:1][C:2]1[N:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)[CH:3]=1.[O:20]1[CH:25]=[CH:24][CH2:23][CH2:22][CH2:21]1.CCCCCCC.CCOC(C)=O>C(Cl)Cl.CC1C=CC(S(O)(=O)=O)=CC=1.O>[Br:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[CH:12][C:13]([C:16]([F:19])([F:17])[F:18])=[CH:14][CH:15]=2)[CH:5]=[C:6]([CH2:8][O:9][CH:21]2[CH2:22][CH2:23][CH2:24][CH2:25][O:20]2)[N:7]=1

Participants

Conditions

Temperature: 23 °C

Procedure

To a solution of the above described [6-bromo-4-(4-trifluoromethyl-phenyl)-pyridin-2-yl]-methanol (4.2 g, 95%, purity 81%) and 3,4-dihydro-2H-pyran (1.4 ml, 15.4 mmol) in DCM (20 ml) at 23° C. was added a catalytic amount of p-TsOH.H2O (10 mg) and the mixture was stirred at 23° C. for 18 h. Then again 3,4-dihydro-2H-pyran (0.7 ml, 7.68 mmol) was added and stirring was continued at 23° C. for another 2 h. The entire reaction mixture was directly subjected to silica gel column chromatography with n-heptane/AcOEt to give the title compound (4.59 g, 100%, 93% purity) as a light yellow oil. MS (ISP) 418.2 [(M+H)+].

Workup

customat 23° C.
stirringstirring
waitwas continued at 23° C. for another 2 h
customThe entire reaction mixture

Sources & evidence

ORD record: ord-770d8dd8f9274c1b9630043dbe579e66
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642264B2

Reaction notes

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