Potassium Carbonate → HCID 58056431, compound

HRID 555668Notes

Reaction equation

HRID 555668 reaction equation
[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]([S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[C:21](Br)[C:20]=2[CH3:26])(=[O:18])=[O:17])[CH:7]=1.[F:28][C:29]([F:41])([F:40])[O:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[K+].[K+]>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.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:27])[CH2:4][CH2:5][C:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([F:15])[CH:13]=2)[N:8]([S:16]([C:19]2[C:20]([CH3:26])=[C:21]([C:34]3[CH:33]=[CH:32][C:31]([O:30][C:29]([F:28])([F:40])[F:41])=[CH:36][CH:35]=3)[CH:22]=[CH:23][CH:24]=2)(=[O:18])=[O:17])[CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 58056555HCID 58056555, compound

Product 1

HCID 58056431HCID 58056431, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

Into a 50 mL oven dried round bottom flask, 3-[1-(3-Bromo-2-methyl-benzenesulfonyl)-5-fluoro-1H-indol-3-yl]-propionic acid methyl ester (5, 52.062 mg, 1.1459E-4 mol), 4-trifluoromethoxy-phenyl boronic acid (6, 35.397 mg, 1.7189E-4 mol) and Tetrakis(triphenylphosphine)palladium(0) (13.24 mg, 1.146E-5 mol) were combined. A volume of 0.3 mL of 1N K2CO3 was added and the reaction was heated to 110° C. for 90 minutes. TLC analysis showed co-elution of product and starting material. Ethyl acetate was added and washed 5× with saturated sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated at reduced pressure. The crude material was purified using prep plate chromatography (7:3 hexane:ethyl acetate) to provide the desired compound (40 mg isolated, 65% yield). 1H NMR consistent with compound structure. MS(ESI) [M+H+]+=536.1 (calculated 535.51).

Workup

  1. customInto a 50 mL oven dried round bottom flask
  2. washwashed 5× with saturated sodium bicarbonate
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated at reduced pressure
  6. customThe crude material was purified

Sources & evidence

ORD record
ord-287fbe5b3c204547be308334582742eb
Source dataset
uspto-grants-2011_11
Patent number
US08053463B2

Reaction notes

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