Cesium carbonate → HCID 86657055, compound

HRID 1253552Notes

Reaction equation

HRID 1253552 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11](Br)[C:12]2[N:13]([N:15]=[CH:16][CH:17]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:19](=[O:26])([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[NH2:20].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.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]>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH:20][C:19](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:12]2[N:13]([N:15]=[CH:16][CH:17]=2)[CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 77922tert-Butyl carbamateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 67374380HCID 67374380, compound

Product 1

HCID 86657055HCID 86657055, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
95 °C

Procedure

6-(benzyloxy)-4-bromopyrazolo[1,5-a]pyridine (150 mg, 0.495 mmol), tert-butyl carbamate (116 mg, 0.990 mmol), tris(dibenzylideneacetone)dipalladium (0) (45.3 mg, 0.049 mmol), Xantphos (57.3 mg, 0.099 mmol), and cesium carbonate (484 mg, 1.48 mmol) were suspended in 1,4-dioxane (5 mL). The mixture was sparged with argon for 10 minutes then heated to 95° C. After 2 h, the reaction mixture was diluted in ethyl acetate, washed with saturated aqueous sodium hydrogen carbonate and brine then dried over sodium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient) to afford tert-butyl [6-(benzyloxy)pyrazolo[1,5-a]pyridin-4-yl]carbamate contaminated with tert-butyl carbamate.

Workup

  1. customThe mixture was sparged with argon for 10 minutes
  2. additionthe reaction mixture was diluted in ethyl acetate
  3. washwashed with saturated aqueous sodium hydrogen carbonate and brine
  4. dry with materialthen dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography on silica gel (ethyl acetate/isohexane gradient)

Sources & evidence

ORD record
ord-ce05a732df9a46bf9d4c3fcb7f8c4612
Source dataset
uspto-grants-2013_06
Patent number
US08455477B2

Reaction notes

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