Potassium Carbonate → HCID 86721898, compound

HRID 1049055Notes

Reaction equation

[CH2:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][C:12]([CH:15]=[C:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:24])=[O:23])[CH2:18][CH2:17]2)=[CH:11][CH:10]=1)(=[O:8])=[O:7])[CH:2]([CH3:4])[CH3:3].[F:26][C:27]([F:37])([F:36])[C:28]1[CH:35]=[CH:34][CH:33]=[CH:32][C:29]=1[CH2:30]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH2:1]([N:5]([CH2:30][C:29]1[CH:32]=[CH:33][CH:34]=[CH:35][C:28]=1[C:27]([F:26])([F:36])[F:37])[S:6]([C:9]1[CH:10]=[CH:11][C:12]([CH:15]=[C:16]2[CH2:21][CH2:20][N:19]([S:22]([CH3:25])(=[O:23])=[O:24])[CH2:18][CH2:17]2)=[CH:13][CH:14]=1)(=[O:8])=[O:7])[CH:2]([CH3:3])[CH3:4]

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of N-isobutyl-4-(1-methanesulfonyl-piperidin-4-ylidenemethyl)-benzenesulfonamide (375 mg, 0.97 mmol), 2-(trifluoromethyl)benzyl bromide (289 mg, 1.22 mmol) and K2CO3 (201 mg, 1.46 mmol) in DMF (5 mL) was heated at 110° C. for 6 hours. The cooled mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4 and concentrated under vacuum. Purification by silica gel column chromatography (0-100% EtOAc in cyclohexane) and concentrating the residue from Et2O gave the title compound (290 mg, 55%). 1H NMR (400 MHz, DMSO) δ 7.83 (d, J=8.3 Hz, 2H), 7.70-7.73 (m, 3H), 7.49 (t, J=8.1 Hz, 3H), 6.51 (s, 1H), 4.46 (s, 2H), 3.22 (dt, J=30.4, 5.7 Hz, 4H), 2.96 (d, J=7.3 Hz, 2H), 2.89 (s, 3H), 2.49-2.50 (m, 4H), 1.39-1.40 (m, 1H), 0.70 (d, J=6.6 Hz, 6H). LCMS (m/z, Method B) ES+ 544.9 [M+1]+.

Workup

washwashed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum
customPurification by silica gel column chromatography (0-100% EtOAc in cyclohexane)
concentrationconcentrating the residue from Et2O

Sources & evidence

ORD record: ord-a11e1697cdf349ee99458174173158e1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382222B2

Reaction notes

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