Cesium carbonate → HCID 58408291, compound

HRID 2192287Notes

Reaction equation

HRID 2192287 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:6][CH:7]=1.CC1(C)C(C)(C)OB([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([S:29]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:24][CH2:23]3)O1.C(=O)([O-])[O-].[Cs+].[Cs+].[B-](F)(F)(F)F.CC([PH+](C(C)(C)C)C(C)(C)C)(C)C>O1CCCC1.C(OCC)(=O)C>[F:9][C:8]([F:11])([F:10])[C:5]1[N:4]=[N:3][C:2]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([S:29]([C:32]2[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[CH:34][CH:33]=2)(=[O:31])=[O:30])[CH2:24][CH2:23]3)=[CH:7][CH:6]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 2734635Tri-tert-butylphosphine tetrafluoroborateHCID 282425263-Chloro-6-(trifluoromethyl)pyridazineHCID 58408293HCID 58408293, compound

Product 1

HCID 58408291HCID 58408291, compoundYield 47.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

394 mg 2-lodo-5-methoxypyridine, 144 mg 3-Chloro-6-trifluormethyl-pyridazine, 323 mg 4-[5-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile, 2.56 g cesium carbonate and 23 mg fluoroboric acid tri-tert-butylphosphine adduct were dissolved in 65 ml tetrahydrofuran. The reaction mixture was degassed with argon and then 88 mg Tris(dibenzylideneacetone)palladium(0) chloroform adduct were added and the mixture heated to 80° C. for two hours. The cooled reaction mixture was diluted with 100 ml ethyl acetate and washed with 50 ml water and brine. The organic layer was dried over MgSO4 and the solvent removed in vacuo. The resulting crude material was purified by purified by chromatography on silica gel to obtain 160 mg 4-[5-(6-Trifluoromethyl-pyridazin-3-yl)-2,3-dihydro-indole-1-sulfonyl]-benzonitrile.

Workup

  1. customThe reaction mixture was degassed with argon
  2. addition88 mg Tris(dibenzylideneacetone)palladium(0) chloroform adduct were added
  3. customThe cooled reaction mixture
  4. washwashed with 50 ml water and brine
  5. dry with materialThe organic layer was dried over MgSO4
  6. customthe solvent removed in vacuo
  7. customThe resulting crude material was purified
  8. customby purified by chromatography on silica gel

Sources & evidence

ORD record
ord-239e09d946944f72b94bbafd0665c9b5
Source dataset
uspto-grants-2012_12
Patent number
US08329725B2

Reaction notes

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