alpha-Methylene butyrolactone → HCID 86655229, compound

HRID 1256160Notes

Reaction equation

[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](I)[CH:7]=1)=[O:4].[CH2:15]=[C:16]1[CH2:20][CH2:19][O:18][C:17]1=[O:21].CC([O-])=O.[K+]>CN1C(=O)CCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:1][C:2]([F:14])([F:13])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8](/[CH:15]=[C:16]2\[C:17](=[O:21])[O:18][CH2:19][CH2:20]\2)[CH:7]=1)=[O:4]

Participants

Conditions

Temperature: 110 °C

Procedure

The reaction mixture of 2,2,2-trifluoro-N-(3-iodophenyl)acetamide (160 mg, 0.52 mmol), 3-methylenedihydrofuran-2(3H)-one (62 mg, 0.63 mmol), Pd(OAc)2 (33 mg, 0.015 mmol) and KOAc (200 mg, 2.04 mmol) in NMP (2 mL) was degassed and heated to 110° C. for 12 hrs. The mixture was extracted with EtOAc and washed with H2O, brine, dried over MgSO4, filtered, concentrated in reduced pressure to dryness, and recrystallized in MeOH to give desired intermediate (Z)-2,2,2-trifluoro-N-(3-((2-oxodihydrofuran-3(2H)-ylidene)methyl)phenyl)acetamide (120 mg). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 11.4 (s, 1H), 7.96 (s, 1H), 7.74 (dt, J=7.6, 1.6 Hz, 1H), 7.51 (7, J=7.6 Hz, 1H), 7.28 (d, J=8.4 Hz, 1H), 7.47 (dt, J=7.6, 1.6 Hz, 1H), 7.38 (t, J=2.8 Hz, 1H), 4.43 (t, J=7.2 Hz, 2H), 3.24 (dt, J=2.8, 7.2 Hz, 2H). MS (ESI) m/z=284 (M−1).

Workup

customwas degassed
extractionThe mixture was extracted with EtOAc
washwashed with H2O, brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in reduced pressure to dryness
customrecrystallized in MeOH

Sources & evidence

ORD record: ord-6b03a9673b464590898dcc2f52b1220d
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08461134B2

Reaction notes

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