Cesium carbonate → HCID 66930609, compound

HRID 1364121Notes

Reaction equation

HRID 1364121 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:17]=[C:16]3[C:10]([CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:15]3)=[N:9]2)=[CH:4][CH:3]=1.[O:25]1[CH2:29][CH2:28][NH:27][C:26]1=[O:30].CC1(C)C2C=CC=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=2OC2C1=CC=CC=2P(C1C=CC=CC=1)C1C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[O:30]=[C:26]1[N:27]([C:2]2[CH:7]=[CH:6][C:5]([N:8]3[CH:17]=[C:16]4[C:10]([CH2:11][CH2:12][N:13]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][CH2:15]4)=[N:9]3)=[CH:4][CH:3]=2)[CH2:28][CH2:29][O:25]1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 739492-OxazolidinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 66931029HCID 66931029, compound

Product 1

HCID 66930609HCID 66930609, compound

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 1,1-dimethylethyl 2-(4-bromophenyl)-4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (150 mg, 0.38 mmol) (may be prepared as described in Description 12), 1,3-oxazolidin-2-one (100 mg, 1.15 mmol), tris(dibenzylideneacetone)dipalladium(0) (18.0 mg, 0.02 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (35.0 mg, 0.06 mmol) and cesium carbonate (195 mg, 0.60 mmol) in dioxan (4 ml) was heated at reflux under argon for 3 hours and then in the microwave for 2 hours at 150° C. The mixture was diluted with ethyl acetate, filtered through celite and washed with 2×20 ml of water. The combined ethyl acetate layers were dried over magnesium sulphate, filtered and evaporated. The crude product was purified by column chromatography eluting with a mixture of ethyl acetate/pentane (50-100%) to afford the product (D26); MS (ES+) m/e 399 [M+H]+.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under argon for 3 hours
  3. filtrationfiltered through celite
  4. washwashed with 2×20 ml of water
  5. dry with materialThe combined ethyl acetate layers were dried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by column chromatography
  9. washeluting with a mixture of ethyl acetate/pentane (50-100%)
  10. customto afford the product (D26)

Sources & evidence

ORD record
ord-ec1438b2bb174a87a3afd373720c81d6
Source dataset
uspto-grants-2011_02
Patent number
US07888347B2

Reaction notes

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