Sodium Carbonate → 4-[3-{6-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester

HRID 418096Notes

Reaction equation

HRID 418096 reaction equation
[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2].[F:41][C:42]1([F:54])[O:46][C:45]2[CH:47]=[CH:48][C:49](B(O)O)=[CH:50][C:44]=2[O:43]1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4](=[O:40])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[C:26]([S:28]([CH3:31])(=[O:30])=[O:29])[CH:25]=[C:24]([C:49]3[CH:48]=[CH:47][C:45]4[O:46][C:42]([F:41])([F:54])[O:43][C:44]=4[CH:50]=3)[CH:23]=2)[C:10]=1[CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH3:2]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 17750030(2,2-Difluoro-1,3-dioxaindan-5-yl)boronic acidHCID 578630554-[3-[6-(3-Bromo-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl Ester

Product 1

HCID 578630564-[3-{6-[3-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-5-methanesulfonyl-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric Acid Ethyl EsterYield 89.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4-[3-[6-(3-bromo-5-methanesulfonyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (1.0 g) in 1,2-dimethoxyethane (80 mL) were added 2,2-difluoro-benzo[1,3]dioxole-5-boronic acid (430 mg), 2 M aq. sodium carbonate solution (3.1 mL) and Pd(PPh3)4 (40 mg) and the resulting mixture was stirred at 85° C. for 3 h. Then the reaction mixture was diluted with ethyl acetate, filtered through Celite and washed with water and brine. The organic extract was dried over anhydrous sodium sulfate, concentrated and purified on a silica gel column using ethyl acetate and hexanes to yield the title compound (1.0 g, 89% yield). HRMS calcd for C37H44O10F2S [M+H]+ 719.2696, observed 719.2693.

Workup

  1. filtrationfiltered through Celite
  2. washwashed with water and brine
  3. extractionThe organic extract
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-e4e99c5966c740f9b8a685fefb107529
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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