Cesium carbonate → HCID 78094611, compound

HRID 632717Notes

Reaction equation

[NH2:1][CH2:2][CH:3]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[C:21]=2Br)[CH2:16][CH2:15]1)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1.[F:28][C:29]1[CH:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH2:1][CH2:2][CH:3]([N:14]1[CH2:19][CH2:18][N:17]([C:20]2[N:25]=[CH:24][N:23]=[C:22]([NH2:26])[C:21]=2[C:32]2[CH:33]=[CH:34][C:29]([F:28])=[CH:30][CH:31]=2)[CH2:16][CH2:15]1)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of 6-{4-[2-Amino-1-(4-trifluoromethyl-phenyl)-ethyl]-piperazin-1-yl}-5-bromo-pyrimidin-4-ylamine (110.00 mg; 0.25 mmol; 1.0 eq.), (4-fluorophenyl)boronic acid (103.7 mg; 0.74 mmol; 3.0 eq.), palladium(2+) acetate (5.5 mg; 0.02 mmol; 0.1 eq.), dicyclohexyl(2′,6′-dimethoxybiphenyl-2-yl)phosphine (20.2 mg; 0.05 mmol; 0.2 eq.) and cesium carbonate (241.4 mg; 0.74 mmol; 3.0 eq.) in dioxane (5.00 ml) and water (0.50 ml) in a sealed tube was stirred at 100° C. overnight. The crude was purified by Reverse Phase chromatography (Waters, basic condition) to afford the title compound as a white solid in 75% yield. LC-MS: (M+1=461, obsd.=461).

Workup

customThe crude was purified by Reverse Phase chromatography (Waters, basic condition)

Sources & evidence

ORD record: ord-74a448d92c14416bb3f76cde2ecaa9bc
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321760B2

Reaction notes

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