Cesium carbonate → HCID 58379054, compound

HRID 1951161Notes

Reaction equation

HRID 1951161 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@@H:13]2[CH3:25])=[N:4][N:3]=1.[C:26]([C:28]1[CH:33]=[CH:32][C:31](B(O)O)=[CH:30][CH:29]=1)#[N:27].C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O>[C:26]([C:28]1[CH:33]=[CH:32][C:31]([C:2]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]([N:12]3[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[CH2:14][C@@H:13]3[CH3:25])=[N:4][N:3]=2)=[CH:30][CH:29]=1)#[N:27]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 27343264-Cyanophenylboronic acidHCID 58379057HCID 58379057, compound

Product 1

HCID 58379054HCID 58379054, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Heat a mixture of (S)-tert-butyl 4-(4-chlorophthalazin-1-yl)-3-methylpiperazine-1-carboxylate (4.0 g, 11.0 mmol), 4-cyanophenylboronic acid (2.43 g, 16.5 mmol), cesium carbonate (14.4 g, 44.1 mmol), and (SP-4-1)-bis[bis(1,1-dimethylethyl)(4-methoxyphenyl)phosphine-κP]dichloro-palladium (J. Org. Chem. 2007, 72, 5104-5112) (75.4 mg, 0.11 mmol) in 1,4-dioxane (80 mL) and water (20 mL) at 90° C. overnight. Partition the reaction mixture between water and CH2Cl2. Extract the aqueous layer with CH2Cl2. Dry the combined organic layer over Na2SO4 and concentrate under reduced pressure. Purify the resulting residue by flash silica gel chromatography (gradient of 0 to 20% EtOAc in CH2Cl2) to provide the title compound as a light orange foam (4.46 g, 94%). ES/MS m/z 430.2 (M+1).

Workup

  1. temperatureHeat
  2. customPartition the reaction mixture between water and CH2Cl2
  3. extractionExtract the aqueous layer with CH2Cl2
  4. dry with materialDry the combined organic layer over Na2SO4
  5. concentrationconcentrate under reduced pressure
  6. customPurify the resulting residue by flash silica gel chromatography (gradient of 0 to 20% EtOAc in CH2Cl2)

Sources & evidence

ORD record
ord-f7d7a62480b545e0bee6ff42fd56564d
Source dataset
uspto-grants-2013_03
Patent number
US08404687B2

Reaction notes

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