Cesium carbonate → HCID 69287986, compound

HRID 2375785Notes

Reaction equation

HRID 2375785 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2].Br[CH2:12][C:13]1[CH:17]=[C:16]([C:18]2[S:19][C:20]([Cl:23])=[CH:21][CH:22]=2)[O:15][N:14]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CC#N.[Br-].C(C(CCCCCCCCCC)(C)C(CCCCCCCCCC)(CCCCCCCCCC)C(CCCCCCCCCC)(CCCCCCCCCC)[PH+](CCCC)CCCC)CCCCCCCCC>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:12][C:13]2[CH:17]=[C:16]([C:18]3[S:19][C:20]([Cl:23])=[CH:21][CH:22]=3)[O:15][N:14]=2)[CH:8]=[CH:9][CH:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 255670Ethyl 1H-pyrrole-2-carboxylateHCID 111501463-Bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole

Product 1

HCID 69287986HCID 69287986, compoundYield 100.6%

Reagents, catalysts & solvents 2

HCID 131727226HCID 131727226, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1H-pyrrole-2-carboxylic acid ethyl ester (70 mg) in MeCN was added 3-bromomethyl-5-(5-chloro-thiophen-2-yl)-isoxazole (139 mg), Cs2CO3 (180 mg), Bu4Nl (2 mg) and hexa-n-decyltri-n-butyl phosphonium bromide (10 mg). The mixture was stirred for 4 h at 60° C., whereupon it was cooled to RT and concentrated in vacuo. The residue was partitioned between water and ethyl acetate. The layers were separated and the aqueous phase was extracted with ethyl acetate. The combined organic phases were dried over anhydrous MgSO4 and concentrated in vacuo to provide 1-[5-(5-chloro-thiophen-2-yl)-isoxazol-3-ylmethyl]-1H-pyrrole-2-carboxylic acid ethyl ester (169 mg) which was directly used in the next step. MS (ESI+): m/e 337 [M+H]+, chloro pattern.

Workup

  1. temperaturewas cooled to RT
  2. concentrationconcentrated in vacuo
  3. customThe residue was partitioned between water and ethyl acetate
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with ethyl acetate
  6. dry with materialThe combined organic phases were dried over anhydrous MgSO4
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3060eec0f53c42a9bc09ccf2ecf39b28
Source dataset
uspto-grants-2008_12
Patent number
US07465806B2

Reaction notes

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