Cesium carbonate → Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-2-methoxy-4-methylbenzoate

HRID 555178Notes

Reaction equation

HRID 555178 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[C:8](B2OC(C)(C)C(C)(C)O2)[C:7]([CH3:19])=[CH:6][C:5]=1[O:20][CH3:21].FC(F)(F)S(O[C:29]1[CH:30]=[CH:31][C:32]2[O:36][C:35]([C:37]3[CH:42]=[CH:41][C:40]([F:43])=[CH:39][CH:38]=3)=[C:34]([C:44](=[O:47])[NH:45][CH3:46])[C:33]=2[CH:48]=1)(=O)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.O.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>[F:43][C:40]1[CH:39]=[CH:38][C:37]([C:35]2[O:36][C:32]3[CH:31]=[CH:30][C:29]([C:8]4[C:7]([CH3:19])=[CH:6][C:5]([O:20][CH3:21])=[C:4]([CH:9]=4)[C:3]([O:2][CH3:1])=[O:22])=[CH:48][C:33]=3[C:34]=2[C:44](=[O:47])[NH:45][CH3:46])=[CH:42][CH:41]=1

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 59224652Methyl 2-methoxy-4-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzoateHCID 59275663(4-Fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate

Product 1

HCID 59275447Methyl 5-(2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl)-2-methoxy-4-methylbenzoate

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

Methyl-2-methoxy-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (1.2 g, 3.92 mmol, 1 eq), 2-(4-fluorophenyl)-3-(methylcarbamoyl)benzofuran-5-yl trifluoromethanesulfonate (1.6 g, 3.92 mmol, 1 eq), Cesium carbonate (3.8 g, 11.7 mmol, 3 eq) and Tetrakis triphenylphosphinepalladium (0.13 g, 0.11 mmol, 0.03 eq) were dissolved in 1,4-dioxane/water and the above solution was stirred at 90° C. for 10 h. Then the reaction mixture was diluted with water and product was extracted with ethyl acetate and purified by combiflash chromatography using 40% ethyl acetate/hexane as eluent. Yield: 0.95 g (55%). 1H NMR (400 MHz, DMSO-d6): δ 2.3 (s, 3H), 2.82 (d, J=4.6 Hz, 3H), 3.78 (s, 3H), 3.88 (s, 3H), 7.15 (s, 1H), 7.51 (s, 1H), 7.64 (m, 2H), 7.65 (m, 2H), 7.74 (d, 1H, J=8.48 Hz), 8.00-8.01 (m, 2H), 8.48 (d, 1H). LCMS: (ES+) m/z=448 (M+H).

Workup

  1. extractionwas extracted with ethyl acetate
  2. custompurified by combiflash chromatography

Sources & evidence

ORD record
ord-e2758662197d4872a4804b7741edec27
Source dataset
uspto-grants-2011_11
Patent number
US08048887B2

Reaction notes

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