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Cesium carbonate → HCID 69009937, compound

HRID 2102410
Notes
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Reaction equation

HRID 2102410 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8][CH3:9])[CH:5]=[CH:4][C:3]=1[NH2:10].C1(P(C2C=CC=CC=2)C2(P(C3C=CC=CC=3)C3C=CC=CC=3)CC=C3C(C=CC=C3)=C2C2C3C(=CC=CC=3)C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:63]([O:65][C:66]([C:68]1[C:73](Cl)=[C:72]([CH3:75])[N:71]2[N:76]=[CH:77][CH:78]=[C:70]2[N:69]=1)=[O:67])[CH3:64]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:63]([O:65][C:66]([C:68]1[C:73]([NH:10][C:3]2[CH:4]=[CH:5][C:6]([S:8][CH3:9])=[CH:7][C:2]=2[F:1])=[C:72]([CH3:75])[N:71]2[N:76]=[CH:77][CH:78]=[C:70]2[N:69]=1)=[O:67])[CH3:64]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 220256172-Fluoro-4-(methylsulfanyl)anilineHCID 69005522HCID 69005522, compoundHCID 86595863(+/-)-2,2-Bis(diphenylphosphino)-1,1-binaphthyl

Product 1

HCID 69009937HCID 69009937, compound

Reagents, catalysts & solvents 3

HCID 167845
palladium(II) acetate
Catalyst
HCID 1140TolueneSolvent
HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoro-4-methylsulfanyl-phenylamine (1.01 equivalents), palladium(II) acetate (0.10 equivalents), rac-2,2-bis(diphenylphosphino)-1,1′-binaphthyl (0.15 equivalents), and cesium carbonate (1.50 equivalents) are added to a solution of 6-chloro-7-methylpyrazolo[1,5-a]pyrimidine-5-carboxylic acid ethyl ester (1.00 equivalent) in toluene in a sealed vial. After stirring 10 minutes, the mixture is heated to 80° C. After 24 hours, the reaction mixture is cooled to room temperature and diluted with EtOAc. The resulting precipitate is filtered and washed with EtOAc. The filtrate is diluted with EtOAc and washed with water. The aqueous layer is re-extracted with EtOAc. The combined organic layers are washed with brine, dried (MgSO4) and concentrated. The product is purified by flash chromatography as necessary.

Workup

  1. waitAfter 24 hours
  2. temperaturethe reaction mixture is cooled to room temperature
  3. filtrationThe resulting precipitate is filtered
  4. washwashed with EtOAc
  5. additionThe filtrate is diluted with EtOAc
  6. washwashed with water
  7. extractionThe aqueous layer is re-extracted with EtOAc
  8. washThe combined organic layers are washed with brine
  9. dry with materialdried (MgSO4)
  10. concentrationconcentrated
  11. customThe product is purified by flash chromatography as necessary

Sources & evidence

ORD record
ord-4249cf1c88a745d69eb36390fbdb178a
Source dataset
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07576072B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes