Cesium carbonate → HCID 58866036, compound

HRID 1010839Notes

Reaction equation

HRID 1010839 reaction equation
Cl[C:2]1[C:7]2=[CH:8][CH:9]=[CH:10][N:6]2[N:5]=[C:4]([C:11]2[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=2[F:18])[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:25]1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.[NH2:71][C:72]1[CH:77]=[CH:76][N:75]=[C:74](C)[CH:73]=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:17][C:15]1[CH:14]=[CH:13][C:12]([F:18])=[C:11]([C:4]2[N:3]=[C:2]([NH:71][C:72]3[CH:73]=[CH:74][N:75]=[CH:76][C:77]=3[CH3:25])[C:7]3=[CH:8][CH:9]=[CH:10][N:6]3[N:5]=2)[CH:16]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7286704-Amino-2-methylpyridineHCID 21104340HCID 21104340, compound

Product 1

HCID 58866036HCID 58866036, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

4-Chloro-2-(5-chloro-2-fluoro-phenyl)-pyrrolo[2,1-f][1,2,4]triazine (30 mg, 0.106 mmole), cesium carbonate (48.5 mg, 0.149 mmole), palladium (II) acetate (1.19 mg, 0.0053 mmole), BINAP (4.96 mg, 0.0080 mmole), and 4-amino-picoline (13.8 mg, 0.128 mmole) were combined in 4 ml dioxane (anh.) and heated to 90° C. with stirring overnight. The reaction mixture was filtered to remove solid material, the filtrate was evaporated to dryness, the residue was dissolved in chloroform (8 ml), washed with 0.5 M sodium hydroxide (1 ml), dried over sodium sulfate (anh.), evaporated to dryness, and then the residue was redissolved in dimethylformamide and purified by reversed phase HPLC. The product was isolated.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto remove solid material
  3. customthe filtrate was evaporated to dryness
  4. dissolutionthe residue was dissolved in chloroform (8 ml)
  5. washwashed with 0.5 M sodium hydroxide (1 ml)
  6. dry with materialdried over sodium sulfate (anh.)
  7. customevaporated to dryness
  8. dissolutionthe residue was redissolved in dimethylformamide
  9. custompurified by reversed phase HPLC
  10. customThe product was isolated

Sources & evidence

ORD record
ord-67c3091ad297458f82dd7589b572c72f
Source dataset
uspto-grants-2011_07
Patent number
US07977342B2

Reaction notes

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