Cesium carbonate → HCID 58016949, compound

HRID 1926968Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17](Br)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1.[F:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1.C(=O)([O-])[O-].[Cs+].[Cs+].P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.CC(O)=O.CC(O)=O.C1CCC([N-]C2CCCCC2)CC1.C1CCC([N-]C2CCCCC2)CC1.[Pd+2]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][NH:9][C:10]1[C:11]2[C:18]([C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:17]([C:34]3[CH:33]=[CH:32][CH:31]=[C:30]([F:29])[CH:35]=3)[O:16][C:12]=2[N:13]=[CH:14][N:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Add 3 mg (0.01 mmol) trans-bis(dicyclohexylamine)palladium(II) acetate [T. Bin, J. Org. Chem. 2004, 69, 4330-4335] to a mixture of 100 mg (0.22 mmol) 6-{[6-bromo-5-(4-methoxyphenyl)furo[2,3-d]pyrimidin-4-yl]amino}hexanoic acid methyl ester, 47 mg (0.34 mmol) 3-fluorophenylboronic acid and 145 mg (0.45 mmol) caesium carbonate in 5 ml dioxan, and stir for 16 h at 80° C. After adding 95 mg (0.45 mmol) potassium phosphate, a further 47 mg (0.34 mmol) 3-fluorophenylboronic acid and a spatula tip of trans-bis(dicyclohexylamin)palladium(II) acetate, stir the reaction mixture for a further 4 h at 80° C. Then filter the reaction mixture and purify directly by preparative RP-HPLC (gradient: water/acetonitrile). 57 mg (53% of theor.) of the desired product is obtained.

Workup

filtrationThen filter the reaction mixture
custompurify directly by preparative RP-HPLC (gradient: water/acetonitrile)

Sources & evidence

ORD record: ord-a505a96b45e4451b975878eacae4b316
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08183246B2

Reaction notes

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