Cesium carbonate → HCID 49805025, compound

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	3,5-Dimethylisoxazole-4-boronic acid	HCID 2734346	—
Reactant	HCID 86647718	HCID 86647718	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water	HCID 962	—
Solvent	Dimethylformamide	HCID 6228	—
Product	HCID 49805025	HCID 49805025	48%

Reaction Steps

Following the procedure in Example 24, 4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinolin-7-yl trifluoromethanesulfonate (225 mg, 0.53 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (114 mg, 0.8 mmol), cesium carbonate (521 mg, 1.6 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) (22 mg, 0.03 mmol) in N,N-dimethylformamide (4 mL) and water (2 mL) gave 4-(4-(3,4-dichlorophenyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)-3,5-dimethylisoxazole (95 mg, 48%) as a brown oil: 1H NMR (CD3OD, 500 MHz) δ 7.46 (d, J=8.3 Hz, 1H), 7.34 (d, J=2.0 Hz, 1H), 7.13-7.08 (m, 3H), 6.92 (d, J=8.0 Hz, 1H), 4.24-4.05 (m, 3H), 3.39 (dd, J=12.9, 5.7 Hz, 1H), 3.01 (dd, J=12.9, 8.3 Hz, 1H), 2.39 (s, 3H), 2.24 (s, 3H); ESI MS m/z 373 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09034899B2
Source dataset	uspto-grants-2015_05
ORD ID	ord-2d8651c3c67d4f48bc420edfbe287734
Source note	uspto-grants-2015_05