Potassium Carbonate → 3-(pyridin-3-yl)-N-(4-((3-(trifluoromethoxy)phenyl)sulfonyl)phenyl)acrylamide

HRID 1754114Notes

Reaction equation

[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:5]=[C:6]([S:10]([C:13]2[CH:19]=[CH:18][C:16]([NH2:17])=[CH:15][CH:14]=2)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30](Cl)=[O:31])[CH:23]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([CH:28]=[CH:29][C:30]([NH:17][C:16]2[CH:18]=[CH:19][C:13]([S:10]([C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:1])([F:20])[F:21])[CH:5]=3)(=[O:12])=[O:11])=[CH:14][CH:15]=2)=[O:31])[CH:23]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-((3-(trifluoromethoxy)phenyl)sulfonyl)aniline (86, 0.27 mmol) in DMF (3 mL) is added 3-(pyridin-3-yl)acryloyl chloride (58 mg, 0.28 mmol) and K2CO3 (138 mg, 1 mmol). The mixture is heated at 50° C. for 2 h and the solvent is evaporated. The residue is partitioned between EtOAc (15 mL) and brine (10 mL) and the layers are separated. The aqueous layer is extracted with EtOAc (10 mL) and the combined extracts are dried (Na2SO4) and evaporated. Purification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH gives the titled compounds as a white solid (60 mg, 50%). (LC_MS: M+1 449.14; 1HNMR (400 MHz, DMSO-d6): δ 10.76 (s, 1H), 8.82 (d, 1H), 8.57 (dd, 1H), 7.89-8.06 (m, 7H), 7.76 (t, 1H), 7.74 (m, 1H), 7.66 (d, 1H), 7.46 (dd, 1H), 6.91 (d, 1H).

Workup

customthe solvent is evaporated
customThe residue is partitioned between EtOAc (15 mL) and brine (10 mL)
customthe layers are separated
extractionThe aqueous layer is extracted with EtOAc (10 mL)
dry with materialthe combined extracts are dried (Na2SO4)
customevaporated
customPurification of the residue by preparative TLC with 100:5:0.5 CH2Cl2/MeOH/NH4OH

Sources & evidence

ORD record: ord-1ea0799775a1465ab2ed108d61c68888
Source dataset: uspto-grants-2015_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09169209B2

Reaction notes

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