Cesium carbonate → HCID 66755860, compound

HRID 1177256Notes

Reaction equation

HRID 1177256 reaction equation
C([O-])([O-])=O.[Cs+].[Cs+].[OH:7][C:8]1[C:13]2[CH:14]=[C:15]([CH3:17])[O:16][C:12]=2[CH:11]=[C:10]([C:18]([O:20]CC)=O)[CH:9]=1.F[C:24]1[CH:29]=[CH:28][C:27]([S:30]([CH3:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1.[CH3:34][N:35]1[CH:39]=[CH:38][C:37]([NH2:40])=[N:36]1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C=O)C>[CH3:33][S:30]([C:27]1[CH:28]=[CH:29][C:24]([O:7][C:8]2[C:13]3[CH:14]=[C:15]([CH3:17])[O:16][C:12]=3[CH:11]=[C:10]([C:18]([NH:40][C:37]3[CH:38]=[CH:39][N:35]([CH3:34])[N:36]=3)=[O:20])[CH:9]=2)=[CH:25][CH:26]=1)(=[O:32])=[O:31]

Participants

7

Reactant 5

HCID 10796Cesium carbonateHCID 679941-Fluoro-4-(methylsulphonyl)benzeneHCID 1372541-Methyl-3-aminopyrazoleHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11514065Ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate

Product 1

HCID 66755860HCID 66755860, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Cs2CO3 (0.806 g, 2.47 mmol) was added to a solution of ethyl 4-hydroxy-2-methylbenzofuran-6-carboxylate (0.273 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 (20 mg, 4% yield) as expected product. 1H NMR (400 MHz, CD3OD) δ 7.99 (m, 1 H) 7.93-7.96 (m, 2 H) 7.56 (m, 1 H) 7.50 (m, 1 H) 7.18-7.20 (m, 2 H) 6.59-6.60 (m, 1 H) 6.33 (s, 1 H) 3.83 (s, 3 H), 3.12 (s, 3 H), 2.47 (s, 3 H). LCMS for C21H19N3O5S m/z 426.10 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-45c947e2ad8f4f168d33607fd30ae8cc
Source dataset
uspto-grants-2010_11
Patent number
US07842713B2

Reaction notes

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