Phosphonium, ((4-methylphenyl)methyl)triphenyl-, bromide (1:1) → 2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-[3-(4methyl-phenyl)propyl]pyridine
Reaction equation
CO[C:3]([C:5]1[C:6]([CH:24]([CH3:26])[CH3:25])=[N:7][C:8]([CH:21]([CH3:23])[CH3:22])=[C:9]([CH2:18][CH:19]=O)[C:10]=1[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:4].[Br-].[CH3:28][C:29]1[CH:54]=[CH:53][C:32]([CH2:33][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:31][CH:30]=1>C(OCC)(=O)C.CCCCCC>[CH:24]([C:6]1[C:5]([CH2:3][OH:4])=[C:10]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:9]([CH2:18][CH2:19][CH2:28][C:29]2[CH:54]=[CH:53][C:32]([CH3:33])=[CH:31][CH:30]=2)=[C:8]([CH:21]([CH3:22])[CH3:23])[N:7]=1)([CH3:26])[CH3:25]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
The title compound was prepared from methyl-2,6-diisopropyl-4-(4-fluorophenyl)-5-(2-oxoethyl)-3-pyridinecarboxylate (Example 82, Step A) and 4-methylbenzyl triphenylphosphonium bromide according to the procedures described in Example 1, Steps F-H. 1H NMR (300 MHz, CDCl3): δ 7.08 (m, 4 H), 7.01 (d, J=8 Hz, 2 H), 6.85 (d, J=8 Hz, 2 H), 4.30 (s, 2 H), 3.39 (sept, J=6.6 Hz, 1 H), 3.13 (sept, J=6.6 Hz, 1 H), 2.41 (t, J=7 Hz, 2 H), 2.31 (s, 3 H), 2.27 (m, 2 H), 1.58 (m, 2 H), 1.31 (d, J=6.6 Hz, 6 H), 1.26 (d, J=6.6 Hz, 6 H), 1.15 (m, 1 H). FAB-MS: calcd for (C28H34FNO) 419, found 420 (M+H). Anal. Calcd for C28H34FNO: C, 80.15; H, 8.17; N, 3.34. Found: C, 80.33; H, 8.28; N, 3.22. mp 79-80° C. Rf=0.4 (20% ethyl acetate/hexane).
Sources & evidence
- ORD record
- ord-bb4bea289c554795abf98ceac614cb51
- Source dataset
- uspto-grants-2001_04
- Patent number
- US06218431B1
Reaction notes
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