Cesium carbonate → HCID 49764912, compound

HRID 1771548Notes

Reaction equation

HRID 1771548 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([N:14]3[CH2:19][CH2:18][O:17][CH2:16][CH2:15]3)[CH:11]=[CH:10][N:9]=2)=[CH:4][CH:3]=1.[CH:20]1([NH:23][C:24](=[O:41])[NH:25]C2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)[CH2:22][CH2:21]1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O.CCOC(C)=O>[CH:20]1([NH:23][C:24]([NH:25][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[N:13]=[C:12]([N:14]4[CH2:19][CH2:18][O:17][CH2:16][CH2:15]4)[CH:11]=[CH:10][N:9]=3)=[CH:4][CH:3]=2)=[O:41])[CH2:22][CH2:21]1

Participants

8

Reactant 3

HCID 10796Cesium carbonateHCID 44119149N-Cyclopropyl-N'-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)ureaHCID 67382293HCID 67382293, compound

Product 1

HCID 49764912HCID 49764912, compoundYield 46%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

4-(2-(4-chlorophenyl)pyrimidin-4-yl)morpholine (100 mg 0.5 mmol), (4-(3-cyclopropylureido)phenyl)boronic acid pinacol ester (181 mg, 0.6 mmol), Cs2CO3 (326 mg, 1.0 mmol) and Pd(PPh3)2Cl2 (18 mg, 0.025 mmol) were combined in dioxane (3 ml) and water 0.7 ml). The reaction mixture was then heated by microwave at 140° C. for 20 min. The reaction mixture was portioned between EtOAc and water. The organic layer was passed through a PTFE hydrophobic frit and the solvent removed in vacuo. The solid residue was triturated with EtOAc, collected by filtration and dried in vacuo to afford the title compound (78 mg, 46%).

Workup

  1. customthe solvent removed in vacuo
  2. customThe solid residue was triturated with EtOAc
  3. filtrationcollected by filtration
  4. customdried in vacuo

Sources & evidence

ORD record
ord-8a124c751c054ee4bd9137c85d911205
Source dataset
uspto-grants-2016_02
Patent number
US09249129B2

Reaction notes

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