Cesium carbonate → HCID 86648128, compound

HRID 2388234Notes

Reaction equation

HRID 2388234 reaction equation
[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][O:16][C:17]2[C:18]4[O:31][N:30]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:19]=4[C:20](I)=[N:21][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.[CH2:38]([B-](F)(F)F)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1.[K+].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH:1]1[C:14]2[C:5](=[CH:6][C:7]3[C:12]([C:13]=2[CH2:15][O:16][C:17]2[C:18]4[O:31][N:30]=[C:29]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)[C:19]=4[C:20]([CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=4)=[N:21][C:22]=2[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 23692459Potassium benzyltrifluoroboranuideHCID 86648127HCID 86648127, compound

Product 1

HCID 86648128HCID 86648128, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

A flask was charged with ethyl 7-(anthracen-9-ylmethoxy)-4-iodo-3-phenylisoxazolo[4,5-c]pyridine-6-carboxylate (200 mg, 0.33 mmol), potassium benzyltrifluoroborate (80 mg, 0.4 mmol), PdCl2(dppf) (27 mg, 0.033 mmol) and cesium carbonate (326 mg, 1.0 mmol). The flask was evacuated and refilled with nitrogen. THF (4 mL) and water (0.4 mL) were added and the mixture was refluxed for 16 h. The solvent was removed in vacuo and the residue was partitioned between EtOAc and 0.5M hydrochloric acid. The aqueous layer was extracted with additional EtOAc and the organic layer was dried over MgSO4. After evaporation of solvent, the crude residue was purified by flash chromatography (0-30% EtOAc/hexanes) to give 110 mg of the title compound. MS: (+) m/z 565.38 (M+1).

Workup

  1. customThe flask was evacuated
  2. additionrefilled with nitrogen
  3. additionTHF (4 mL) and water (0.4 mL) were added
  4. temperaturethe mixture was refluxed for 16 h
  5. customThe solvent was removed in vacuo
  6. customthe residue was partitioned between EtOAc and 0.5M hydrochloric acid
  7. extractionThe aqueous layer was extracted with additional EtOAc
  8. dry with materialthe organic layer was dried over MgSO4
  9. customAfter evaporation of solvent
  10. customthe crude residue was purified by flash chromatography (0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-842fa25d33484983a4f783bb86de8136
Source dataset
uspto-grants-2012_09
Patent number
US08269008B2

Reaction notes

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