Triethylamine → HCID 21196490, compound

HRID 1067135Notes

Reaction equation

HRID 1067135 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH:14]2[CH2:18][CH2:17][CH:16]=[C:15]2[C:19]2[O:20][C:21]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[N:23]=2)[CH:8]=1)(=O)=O.[CH3:38][O:39][C:40]([C:42]1[CH:43]=[C:44](B(O)O)[CH:45]=[CH:46][CH:47]=1)=[O:41].C(N(CC)CC)C>CN(C=O)C.CCOC(C)=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>[C:24]1([C:22]2[N:23]=[C:19]([C:15]3[CH:14]([CH2:13][C:9]4[CH:10]=[C:11]([C:44]5[CH:45]=[CH:46][CH:47]=[C:42]([C:40]([O:39][CH3:38])=[O:41])[CH:43]=5)[CH:12]=[CH:7][CH:8]=4)[CH2:18][CH2:17][CH:16]=3)[O:20][C:21]=2[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 27347143-(Methoxycarbonyl)benzeneboronic acidHCID 21196465HCID 21196465, compound

Product 1

HCID 21196490HCID 21196490, compoundYield 68%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]methyl}phenyl trifluoromethanesulfonate (400 mg), 3-methoxycarbonylphenylboronic acid (177 mg), triethylamine (0.318 ml), and tetrakis(triphenylphosphine)palladium(0) (64 mg) in DMF (8 ml) was stirred at 100° C. for 3.5 hours. After cooling to room temperature, the reaction mixture was diluted with EtOAc, washed with water, 1N HCl, water, saturated sodium hydrogen carbonate, water, and brine, dried over magnesium sulfate, evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane-EtOAc 10:1) to give methyl 3′-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclopenten-1-yl]-methyl}biphenyl-3-carboxylate (264.6 mg) as an oil.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed with water, 1N HCl, water, saturated sodium hydrogen carbonate, water, and brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by silica gel column chromatography (hexane-EtOAc 10:1)

Sources & evidence

ORD record
ord-ddd4f75cb449436b8412e5e66afa1f6f
Source dataset
uspto-grants-2001_06
Patent number
US06245790B1

Reaction notes

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