Potassium Carbonate → HCID 69324168, compound

HRID 448089Notes

Reaction equation

Br[C:2]1[S:6]/[C:5](=[CH:7]\[C:8]([C:10]2[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=2[O:17][CH3:18])=[O:9])/[N:4]([CH2:19][CH2:20][CH2:21][CH3:22])[C:3]=1[CH3:23].[F:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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>[CH2:19]([N:4]1[C:3]([CH3:23])=[C:2]([C:28]2[CH:29]=[CH:30][C:25]([F:24])=[CH:26][CH:27]=2)[S:6]/[C:5]/1=[CH:7]\[C:8]([C:10]1[CH:15]=[C:14]([Cl:16])[CH:13]=[CH:12][C:11]=1[O:17][CH3:18])=[O:9])[CH2:20][CH2:21][CH3:22]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of the product from Example 13 (126 mg, 0.3 mmol), 4-fluorophenylboronic acid (45 mg, 0.3 mmol0, triphenylphosphine (79 mg, 0.3 mmol), potassium carbonate (69 mg, 0.5 mmol) and Pd(Ph3P)4 (35 mg, 0.03 mmol) in dioxane (10 mL) was refluxed at 80° C. for 48 min. The mixture was then cooled to room temperature and concentrated under reduced pressure. The residue was purified by chromatography (hexane-EtOAc 2:1) to afford 50 mg of the title compound. 1H NMR (300 MHz, DMSO-d6) δ 0.95 (t, J=7 Hz, 3H), 1.44 (sextet, J=7 Hz, 2H), 1.74 (quintet, J=7 Hz, 2H), 2.32 (s, 3H), 3.87 (s, 3H), 4.02 (t, J=7 Hz, 2H), 6.68 (s, 1H), 7.13 (d, J=9 Hz, 1H), 7.33 (t, J=9 Hz, 2H), 7.47 (m, 3H), 7.66 (d, J=3 Hz, 1H); MS (ESI) m/z 432 (M+H)+. Anal calcd for C23H23ClFNO2S.0.25H2O: C, 63.29; H, 5.43; N, 3.21. Found: C, 63.20; H, 5.25; N, 3.04.

Workup

temperatureThe mixture was then cooled to room temperature
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography (hexane-EtOAc 2:1)

Sources & evidence

ORD record: ord-4795fac6399941c6b177646d0df9b452
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08481574B2

Reaction notes

Loading…