2-Methyl-4-phenyl-1,3-thiazole → 4-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane

HRID 1855040Notes

Reaction equation

HRID 1855040 reaction equation
[I:1][CH2:2][C:3]12[CH2:10][CH2:9][C:6]([C:11]3SC(C)=N[C:12]=3[C:17]3[CH:22]=[CH:21][CH:20]=CC=3)([CH2:7][CH2:8]1)[O:5][CH2:4]2.CC1SC=C(C2C=CC=CC=2)N=1.BrC1C=C(C=CC=1)[O:39][CH:40]1[CH2:45][CH2:44][CH2:43][CH2:42][O:41]1>>[I:1][CH2:2][C:3]12[CH2:8][CH2:7][C:6]([C:11]3[CH:20]=[CH:21][CH:22]=[C:17]([O:39][CH:40]4[CH2:45][CH2:44][CH2:43][CH2:42][O:41]4)[CH:12]=3)([CH2:9][CH2:10]1)[O:5][CH2:4]2

Participants

4

Reactant 3

HCID 5843772-Methyl-4-phenyl-1,3-thiazoleHCID 50672642-(3-Bromophenoxy)tetrahydro-2H-pyranHCID 904086535-(4-(Iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole

Product 1

HCID 904096954-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane

Procedure

4-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane was prepared using a procedure analogous to 5-(4-(iodomethyl)-2-oxabicyclo[2.2.2]octan-1-yl)-2-methyl-4-phenylthiazole except that 2-methyl-4-phenylthiazole was replaced with 2-(3-bromophenoxy)tetrahydro-2H-pyran. The title compound was obtained (1.2 g, 2.80 mmol, 100% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ 7.24 (t, J=8.0 Hz, 1H), 7.14-7.11 (m, 1H), 7.02 (ddd, J=7.8, 1.6, 1.0 Hz, 1H), 6.96 (ddd, J=8.2, 2.5, 0.9 Hz, 1H), 5.45 (t, J=3.2 Hz, 1H), 4.00-3.87 (m, 3H), 3.62 (dtd, J=11.3, 4.1, 1.2 Hz, 1H), 3.08 (s, 2H), 2.16-1.98 (m, 5H), 1.93-1.58 (m, 9H).

Workup

  1. custom4-(Iodomethyl)-1-(3-(tetrahydro-2H-pyran-2-yloxy)phenyl)-2-oxabicyclo[2.2.2]octane was prepared

Sources & evidence

ORD record
ord-bc0085e7357a47bdb69cd2c016b0dbaa
Source dataset
uspto-grants-2015_02
Patent number
US08962660B2

Reaction notes

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