Cesium carbonate → HCID 58552862, compound

https://huagongshe.com/reaction/520454

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl	HCID 11155794	—
Reactant	Potassium trifluoro[(pyrrolidin-1-yl)methyl]borate	HCID 45588176	—
Reactant	HCID 58552853	HCID 58552853	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Water	HCID 962	—
Product	HCID 58552862	HCID 58552862	63%

Reaction Conditions

Temperature	150 °C

Reaction Steps

Degassed THF/H2O (4 mL, 10:1) was added to a microwave vial containing 2-(4-bromophenyl)-3-methyl-4-oxo-N-(pyridin-2-yl)-3,4-dihydroquinazoline-8-carboxamide 28 (100 mg, 0.23 mmol), Cs2CO3 (224 mg, 0.69 mmol), Pd(OAc)2 (1.5 mg, 0.007 mmol), XPHOS (65 mg, 0.014 mmol), and potassium 1-trifluoroboratomethylpyrrolidine (48 mg, 0.25 mmol). The reaction mixture was heated at 150° C. in a microwave reactor for 30 min., poured into H2O and extracted with EtOAc. The combined organics were washed with brine, dried, concentrated and the crude residue purified by MPLC eluting with CH2Cl2/MeOH (0-10%) to give Compound 275 (63 mg, 63% yield). MS (ESI) calc. for C26H25N5O2: 439.20. found: 440 [M+H].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09326986B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-5633d2f86e694a4185024f6c053a5484
Source note	uspto-grants-2016_05