Triethylamine → 2-Acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl ester

HRID 906527Notes

Reaction equation

HRID 906527 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8](I)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17].C([Sn](CCCC)(CCCC)[C:25]1[O:26][CH2:27][CH2:28][CH:29]=1)CCC.CCN(CC)CC>O1CCOCC1.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>[CH3:1][O:2][C:3](=[O:19])[C:4]1[CH:9]=[C:8]([C:25]2[O:26][CH2:27][CH2:28][CH:29]=2)[C:7]([C:11]([F:14])([F:13])[F:12])=[CH:6][C:5]=1[NH:15][C:16](=[O:18])[CH3:17]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 14323397Tributyl(4,5-dihydrofuran-2-yl)stannaneHCID 591644332-Acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester

Product 1

HCID 585329042-Acetylamino-5-(4,5-dihydro-furan-2-yl)-4-trifluoromethyl-benzoic acid methyl esterYield 86%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-acetylamino-5-iodo-4-trifluoromethyl-benzoic acid methyl ester (10 g, 25.8 mmol) in dioxane were added tributyl-(4,5-dihydro-furan-2-yl)-stannane (13.9 g, 38.7 mmol), (Ph3P)4Pd then Et3N (4.52 mL, 32.3 mmol). The reaction mixture was heated at reflux for 18 h to give a brown suspension that was allowed to cool to r.t. The reaction mixture was filtered through a sintered funnel and the filtrate was concentrated under in vacuo. The residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes) to give the title compound (7.3 g, 86%) as beige crystals, m.p.: 120-125° C., API-ES: m/z 330 [M+H]+

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 18 h
  3. customto give a brown suspension that
  4. filtrationThe reaction mixture was filtered through a sintered funnel
  5. concentrationthe filtrate was concentrated under in vacuo
  6. customThe residue was purified by flash column chromatography (silica gel, 1:4 EtOAc/hexanes)

Sources & evidence

ORD record
ord-aeaeb6b63d034ea595b16b23f43b65a1
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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