2,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine → HCID 53749508, compound

HRID 324832Notes

Reaction equation

HRID 324832 reaction equation
[CH:1]([C:4]1[C:9]([CH2:10][OH:11])=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:26])[CH3:25])[N:5]=1)([CH3:3])[CH3:2].[CH2:27]([Mg]Br)[CH:28]=[CH2:29]>C(Cl)Cl.CCCCCC>[CH:1]([C:4]1[C:9]([CH:10]([OH:11])[CH:27]=[CH:28][CH3:29])=[C:8]([C:12]2[CH:13]=[CH:14][C:15]([F:18])=[CH:16][CH:17]=2)[C:7]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[C:6]([CH:24]([CH3:25])[CH3:26])[N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 220049552,6-Diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridineHCID 178455850HCID 178455850, compound

Product 1

HCID 53749508HCID 53749508, compound

Reagents, catalysts & solvents 1

HCID 21226440Methylenechloride HexaneSolvent

Procedure

The title compound was prepared from 2,6-diisopropyl-3-hydroxymethyl-4-(4-fluorophenyl)-5-pentylpyridine (Example 1) and allylmagnesium bromide according to the procedures described in Example 114. 1H NMR (300 MHz, CDCl3): δ 7.09 (m, 4 H), 6.58 (m, 1 H), 5.06 (s, 1 H), 5.01 (m, 1 H), 4.47 (m, 1 H), 3.71 (septet, J=6.6 Hz, 1 H), 3.20 (septet, J=6.6 Hz, 1 H), 2.59 (m, 1 H), 2.35 (m, 1 H), 2.18 (t, J=4.8 Hz, 2 H), 1.72 (d, J=2.9 Hz, 1 H), 1.28 (m, 14 H), 1.11 (m, 4 H), 0.783 (t, J=6.6 Hz, 3 H). FAB-MS: calcd for (C26H36FNO) 397, found 398 (M+H). Anal. Calcd for C26H36FNO: C, 77.88; H, 9.41; N, 3.63; F, 4.93. Found: C, 78.10; H, 9.21; N, 3.43; F, 4.89. mp 70-72° C. Rf=0.2 (50% CH2Cl2/hexane).

Sources & evidence

ORD record
ord-7f84fd71aaae462cbf0c37e283b7cc00
Source dataset
uspto-grants-2001_04
Patent number
US06218431B1

Reaction notes

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