Cesium carbonate → HCID 68295583, compound

HRID 1406021Notes

Reaction equation

HRID 1406021 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[C:8]3[N:15]([CH3:16])[N:14]=[C:13]([C:17]([NH:19][C:20]4[C:25]([CH2:26][CH3:27])=[CH:24][CH:23]=[CH:22][C:21]=4[CH2:28][CH3:29])=[O:18])[C:9]=3[CH2:10][CH2:11][CH2:12][C:5]2=[CH:4][N:3]=1.I[C:31]1[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[CH:33][C:32]=1[O:44][CH3:45].C([O-])([O-])=O.[Cs+].[Cs+].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>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]>[CH2:26]([C:25]1[CH:24]=[CH:23][CH:22]=[C:21]([CH2:28][CH3:29])[C:20]=1[NH:19][C:17]([C:13]1[C:9]2[CH2:10][CH2:11][CH2:12][C:5]3[C:6](=[N:7][C:2]([NH:1][C:31]4[CH:43]=[CH:42][C:34]([C:35]([O:37][C:38]([CH3:40])([CH3:41])[CH3:39])=[O:36])=[CH:33][C:32]=4[O:44][CH3:45])=[N:3][CH:4]=3)[C:8]=2[N:15]([CH3:16])[N:14]=1)=[O:18])[CH3:27]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 60150942HCID 60150942, compoundHCID 66678559HCID 66678559, compound

Product 1

HCID 68295583HCID 68295583, compoundYield 84%

Reagents, catalysts & solvents 2

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

Procedure

To a solution of 9-amino-N-(2,6-diethylphenyl)-1-methyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxamide (0.375 mg, 0.96 mmol) in dioxane (10 mL), tert-butyl 4-iodo-3-methoxybenzoate (0.320 mg, 0.96 mmol) and Cs2CO3 (0.470 g, 1.44 mmol) were added and the flask was evacuated and backfilled with argon. Pd2(dba)3 (0.088 g, 0.096 mmol) and Xantphos (0.110 g, 0.192 mmol) were then charged and the mixture was refluxed under argon for 4 h. After cooling to room temperature, the reaction mixture was concentrated, suspended in water (50 mL) and extracted with AcOEt. The organic phase was anidrified on Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: hexane/AcOEt 8/2) to afford 0.480 g (84% yield) of the title compound.

Workup

  1. customthe flask was evacuated
  2. temperaturethe mixture was refluxed under argon for 4 h
  3. concentrationthe reaction mixture was concentrated
  4. extractionextracted with AcOEt
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customthe crude solid was purified by flash chromatography on silica gel (eluant: hexane/AcOEt 8/2)

Sources & evidence

ORD record
ord-1136ceb0a8cc4f418479cd91dacbe8d3
Source dataset
uspto-grants-2014_12
Patent number
US08916577B2

Reaction notes

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