Cesium carbonate → HCID 86702813, compound

HRID 1850048Notes

Reaction equation

HRID 1850048 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[NH:7]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:15])[CH:9]=[N:8]1.Br[CH2:32][CH2:33][O:34][C:35]1[CH:40]=[C:39]([F:41])[CH:38]=[C:37]([Cl:42])[CH:36]=1>CN(C=O)C.CCOC(C)=O>[Cl:42][C:37]1[CH:36]=[C:35]([CH:40]=[C:39]([F:41])[CH:38]=1)[O:34][CH2:33][CH2:32][N:7]1[CH:11]=[C:10](/[CH:12]=[CH:13]/[C:14]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:15])[CH:9]=[N:8]1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 68294368HCID 68294368, compoundHCID 68349180HCID 68349180, compound

Product 1

HCID 86702813HCID 86702813, compoundYield 95.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Cesium carbonate (98 mg, 0.30 mmol) was added to a solution of (E)-tert-butyl (2-(3-(1H-pyrazol-4-yl)acrylamido)phenyl)carbamate (100 mg, 0.30 mmol) in anhydrous DMF (4 mL). A solution of 1-(2-bromoethoxy)-3-chloro-5-fluorobenzene (76 mg, 0.30 mmol) in DMF (1 mL) was then added and the reaction mixture was stirred overnight at room temperature under a nitrogen atmosphere. It was diluted with EtOAc (30 mL) and washed with water (2×40 mL) and brine (10 mL). The organic layer was dried over anhydrous Na2SO4 and filtered. The evaporated crude was purified by silica gel column chromatography using a gradient of 0-100% of EtOAc in hexanes to provide 144 mg of (E)-tert-butyl (2-(3-(1-(2-(3-chloro-5-fluorophenoxy)ethyl)-1H-pyrazol-4-yl)acrylamido)phenyl)carbamate as a white solid. MS: ES+(M+Na)+: 523

Workup

  1. washwashed with water (2×40 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customThe evaporated crude
  5. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1f42e349f7134acab2e589f2e2833e9b
Source dataset
uspto-grants-2015_02
Patent number
US08957066B2

Reaction notes

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