Cesium carbonate → HCID 53357945, compound

HRID 1500772Notes

Reaction equation

HRID 1500772 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=23)[CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH2:22].C(=O)([O-])[O-].[Cs+].[Cs+].C1(C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C(=CC=CC=2)C=CC=1P(C1C=CC=CC=1)C1C=CC=CC=1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(OCC)(=O)C.C1(C)C=CC=CC=1>[CH3:19][C:20]([CH3:24])([CH3:23])[CH2:21][NH:22][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[N:10][N:11]3[CH:16]=[CH:15][C:14]([C:17]#[N:18])=[CH:13][C:12]=23)[CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 79882NeopentylamineHCID 634876Binap, (A+-)-HCID 86691789HCID 86691789, compound

Product 1

HCID 53357945HCID 53357945, compoundYield 35.5%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

An oven dried resealable Schlenk tube was charged with 3-(6-chloropyridin-2-yl)pyrazolo[1,5-a]pyridine-5-carbonitrile (Preparation 6, 30 mg, 0.12 mmol), (2,2-dimethylpropyl)amine (14 μL, 0.12 mmol), cesium carbonate (77 mg, 0.24 mmol), 1,1-binaphthalene-2,2′-diylbis(diphenylphosphine) (3 mg) and toluene (1.5 mL). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon and palladium (II) acetate (5 mg) was added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 120° C. and stirred for 16 h. The mixture was then cooled and ethyl acetate was added. The organic layer was washed with water, dried (MgSO4) and the solvents were evaporated. Purification of the residue by flash chromatography (dichloromethane to 150:1 dichloromethane/methanol) gave the title compound (13 mg, 34%) as a yellow solid.

Workup

  1. customAn oven dried resealable Schlenk tube
  2. additionwas added
  3. customAfter three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped
  4. customplaced in an oil bath at 120° C.
  5. temperatureThe mixture was then cooled
  6. washThe organic layer was washed with water
  7. dry with materialdried (MgSO4)
  8. customthe solvents were evaporated
  9. customPurification of the residue by flash chromatography (dichloromethane to 150:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-6eef545b4cc249d9aba573c3e197035f
Source dataset
uspto-grants-2015_12
Patent number
US09206183B2

Reaction notes

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