1,10-Phenanthroline → HCID 58497172, compound

HRID 1254072Notes

Reaction equation

HRID 1254072 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17]([CH2:20][CH3:21])[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3[N:32]=CON=3)=[CH:24][CH:23]=2)=[CH:4][CH:3]=1.[CH:33]1(B(O)O)CC1.C([O-])([O-])=O.[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>O1CCOCC1.CN(C1C=CN=CC=1)C.CC([O-])=O.CC([O-])=O.[Cu+2].O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:19]=[CH:18][N:17]([CH:20]4[CH2:21][CH2:33]4)[N:16]=3)=[N:11][C:10]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:32])=[CH:24][CH:23]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 4

HCID 13181,10-PhenanthrolineHCID 10796Cesium carbonateHCID 2760897Cyclopropylboronic acidHCID 58497238HCID 58497238, compound

Product 1

HCID 58497172HCID 58497172, compoundYield 36.3%

Reagents, catalysts & solvents 4

HCID 8895Cupric acetateCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

To a mixture of Step 2 product of Example 140 (150 mg, 0.383 mmol), cyclopropyl boronic acid (132 mg, 1.53 mmol) and Cu(II) acetate (139 mg, 0.766 mmol) in dioxane (2.0 ml) were added DMAP (187 mg, 1.53 mmol), Cs2CO3 (125 mg, 0.383 mmol) and 1,10-phenanthroline (276 mg, 1.53 mmol) in a sealed tube under N2, stirred at rt for 30 min and then heated at 90° C. for overnight. Reaction mixture was diluted water, extracted with EtOAc, washed with brine and dried over Na2SO4, filtered, concentrated, and separated by prep TLC (hex:EtOAc=2:1) to afford 4-{5-[(4-chlorophenyl)sulfanyl]-2-(1-cyclopropyl-1H-pyrazol-3-yl)-1-methyl-1H-imidazol-4-yl}benzonitrile (60 mg) as white solid. LCMS: [M+1]+=432.0.

Workup

  1. temperatureheated at 90° C. for overnight
  2. customReaction mixture
  3. extractionextracted with EtOAc
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customseparated by prep TLC (hex:EtOAc=2:1)

Sources & evidence

ORD record
ord-24d40ae15972419ba7f69823660ffb2d
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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