Cesium carbonate → HCID 11503895, compound

HRID 1994129Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([OH:18])[CH:13]=2)=[CH:4][C:3]=1[C:20]([F:23])([F:22])[F:21].Cl[C:25]1[CH:30]=[CH:29][N:28]=[C:27]([C:31]([NH:33][CH3:34])=[O:32])[CH:26]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:19])[CH2:10][CH2:11][C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[O:18][C:25]2[CH:30]=[CH:29][N:28]=[C:27]([C:31]([NH:33][CH3:34])=[O:32])[CH:26]=2)=[CH:4][C:3]=1[C:20]([F:21])([F:22])[F:23]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of N-[4-chloro-3-(trifluoromethyl)phenyl]-3-(3-hydroxyphenyl)propanamide (585 mg, 1.70 mmol), 4-chloro-N-methylpyridine-2-carboxamide (318 mg, 1.87 mmol), and Cs2CO3 (7.76 g, 8.5 mmol) in DMF (3.4 mL) was heated at 100° C. overnight. The reaction mixture was concentrated and diluted with EtOAc. The organic solution was washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified by column chromatography (SiO2, 0-30% EtOAc in hexanes) to give the product as a white solid. 1H NMR (400 MHz, CD3OD) δ: 8.62 (d, 1H), 8.26 (m, 1H), 7.89-7.96 (m, 1H), 7.71-7.74 (m, 1H), 7.63 (t, 1H), 7.41-7.47 (m, 1H), 7.28 (br s, 1H), 7.17-7.24 (m, 2H), 2.58 (t, 2H), 3.15 (s, 3H), and 2.93 (t, 2H). LCMS, AA: Rt=2.05 min, [MH+ 478.3].

Workup

concentrationThe reaction mixture was concentrated
additiondiluted with EtOAc
washThe organic solution was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography (SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-7ebaf1a226e3447aa0996c6d832869d6
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652041B2

Reaction notes

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