N-Hydroxyphthalimide → 6-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

HRID 1392286Notes

Reaction equation

HRID 1392286 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:8]([O:11][CH2:12][CH2:13][CH2:14]Br)=[CH:9][CH:10]=1)=[O:4].[OH:26][N:27]1[C:31](=[O:32])[C:30]2=[CH:33][CH:34]=[CH:35][CH:36]=[C:29]2[C:28]1=[O:37].C(N(CC)C(C)C)(C)C>>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:16]2[CH:21]=[CH:20][C:19]([C:22]([F:25])([F:24])[F:23])=[CH:18][CH:17]=2)[C:8]([O:11][CH2:12][CH2:13][CH2:14][O:26][N:27]2[C:31](=[O:32])[C:30]3[C:29](=[CH:36][CH:35]=[CH:34][CH:33]=3)[C:28]2=[O:37])=[CH:9][CH:10]=1)=[O:4]

Participants

4

Reactant 3

HCID 10665N-HydroxyphthalimideHCID 81531DiisopropylethylamineHCID 691956816-(3-Bromo-propoxy)-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester

Product 1

HCID 691957396-[3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4'-trifluoromethyl-biphenyl-3-carboxylic acid methyl esterYield 70%

Procedure

This compound was produced using similar methods as those used in Step 1, example 4, starting with 6-(3-bromo-propoxy)-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.60 g, 1.46 mmol), N-hydroxyphthalimide (0.30 g, 1.86 mmol) and N,N-diisopropylethylamine (0.36 g, 2.88 mmol). The crude material was purified by flash chromatography through silica gel using methylene chloride to give 6-[3-(1,3-dioxo-1,3-dihydro-isoindol-2-yloxy)-propoxy]-4′-trifluoromethyl-biphenyl-3-carboxylic acid methyl ester (0.50 g, 70%) as a white solid. 1H NMR (400 MHz, DMSO-d6); δ 8.01 (dd, 1H), 7.88 (d, 1H), 7.84 (s, 4H), 7.74 (s, 4H), 7.31 (d, 1H), 4.31 (t, 2H), 4.22 (t, 2H), 3.82 (s, 3H), 2.09 (m, 2H).

Workup

  1. customThis compound was produced
  2. customThe crude material was purified by flash chromatography through silica gel

Sources & evidence

ORD record
ord-f5549045c2464f08a17ba7887cf18ac8
Source dataset
uspto-grants-2008_03
Patent number
US07342039B2

Reaction notes

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