5-Bromo-2-fluoropyridine → 3-(6-Fluoropyridine-3-yl)-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-ol

HRID 1272335Notes

Reaction equation

HRID 1272335 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH2:14][CH2:13][N:12]([C:15]3[C:16]([CH3:29])=[C:17]([CH3:28])[C:18]4[O:22][C:21]([CH3:24])([CH3:23])[C:20](=[O:25])[C:19]=4[C:26]=3[CH3:27])[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[C:31]1[CH:32]=[CH:33][C:34]([F:37])=[N:35][CH:36]=1>>[F:37][C:34]1[N:35]=[CH:36][C:31]([C:20]2([OH:25])[C:19]3[C:26]([CH3:27])=[C:15]([N:12]4[CH2:11][CH2:10][N:9]([C:6]5[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=5)[CH2:14][CH2:13]4)[C:16]([CH3:29])=[C:17]([CH3:28])[C:18]=3[O:22][C:21]2([CH3:24])[CH3:23])=[CH:32][CH:33]=1

Participants

3

Reactant 2

HCID 27831685-Bromo-2-fluoropyridineHCID 229355955-[4-(4-methoxyphenyl)piperazin-1-yl]-2,2,4,6,7-pentamethyl-1-benzofuran-3(2H)-one

Product 1

HCID 588473313-(6-Fluoropyridine-3-yl)-5-(4-(4-methoxyphenyl)piperazin-1-yl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-olYield 67%

Procedure

Using 4-(4-methoxyphenyl)-1-(2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-3-on-5-yl)piperazine and 5-bromo-2-fluoropyridine obtained in Reference Example 13, the title compound was obtained in the same manner as in Example 33. Yield 67% mp. 129–131° C. (hexane-ethyl acetate).

Workup

  1. customobtained in Reference Example 13

Sources & evidence

ORD record
ord-a15879dd9874455a8fe9c8121c092aa1
Source dataset
uspto-grants-2007_04
Patent number
US07208495B2

Reaction notes

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