Cesium carbonate → 4-(4-(Methylsulfonyl)phenoxy)-N-(1-methyl-1H-pyrazol-3-yl)benzofuran-6-carboxamide

HRID 1177313Notes

Reaction equation

C([O-])([O-])=O.[Cs+].[Cs+].C(O[C:10]([C:12]1[CH:20]=[C:19]([OH:21])[C:15]2[CH:16]=[CH:17][O:18][C:14]=2[CH:13]=1)=[O:11])C.F[C:23]1[CH:28]=[CH:27][C:26]([S:29]([CH3:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1.[CH3:33][N:34]1[CH:38]=[CH:37][C:36]([NH2:39])=[N:35]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:32][S:29]([C:26]1[CH:27]=[CH:28][C:23]([O:21][C:19]2[C:15]3[CH:16]=[CH:17][O:18][C:14]=3[CH:13]=[C:12]([C:10]([NH:39][C:36]3[CH:37]=[CH:38][N:34]([CH3:33])[N:35]=3)=[O:11])[CH:20]=2)=[CH:24][CH:25]=1)(=[O:31])=[O:30]

Participants

Conditions

Temperature: 120 °C

Procedure

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxybenzofuran-6-carboxylate (8a) (0.27 g, 1.24 mmol) and 1-fluoro-4-(methylsulfonyl)benzene (0.22 g, 1.26 mmol) in DMF (5 mL). The mixture was stirred at 120° C. for 8 hours and then cooled to room temperature. 1-Methyl-1H-pyrazol-3-amine (0.18 g, 1.85 mmol) and HATU (0.7 g, 1.85 mmol) were added. The reaction mixture was stirred at 50° C. for one hour and then filtered. Purification by HPLC gave a solid (103 mg, 21% yield) as the expected product. 1H NMR (400 MHz, DMSO-d6) δ 10.97 (s, 1 H) 8.24-8.26 (m, 1 H) 8.17-8.19 (m, 1 H) 7.92-7.97 (m, 2 H) 7.65-7.67 (m, 1 H) 7.60-7.61 (m, 2 H) 7.25-7.29 (m, 1 H) 6.87-6.88 (m, 1 H) 6.58 (m, 1 H) 3.78 (s, 3 H), 3.21 (s, 3 H), 2.58 (m, 3 H). LCMS for C20H17N3O5S m/z 412.10 (M+H)+.

Workup

temperaturecooled to room temperature
stirringThe reaction mixture was stirred at 50° C. for one hour
filtrationfiltered
customPurification by HPLC

Sources & evidence

ORD record: ord-1c9b6f98ce3b4b578d47e2ffc24979d3
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842713B2

Reaction notes

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