Sodium Carbonate → 7-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	Phenylboronic Acid	HCID 66827	—
Reactant	5-Chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one	HCID 59713873	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	7-Fluoro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one	HCID 44366179	76%

Reaction Steps

As illustrated in the scheme above and following General Procedure 4, 5-chloro-7-fluoro-1,3-dihydro-1-methyl-2H-1,4-benzodiazepin-2-one (0.201 g, 0.887 mmol), Na2CO3 (0.0940 g, 0.887 mmol), PdCl2(dppf) (0.0362. g, 0.0443 mmol) and phenylboronic acid (0.108 g, 0.886 mmol) were combined and heated for 13 h. After workup, purification of the crude product by silica gel column chromatography (3:1 CH2Cl2:EtOAc) provided the title compound (0.180 g, 76%). 1H-NMR (CDCl3): δ 7.64-7.60 (m, 2H), 7.51-7.45 (m, 1H), 7.44-7.39 (m, 2H), 7.34 (dd, J=4.8 Hz, J=9.2 Hz, 1H), 7.31-7.25 (m, 1H), 7.02 (dd, J=2.8 Hz, J=8.8 Hz, 1H), 4.84 (d, J=10.8 Hz, 1H), 3.78 (d, J=10.8 Hz, 1H), 3.40 (s, 3H). MS (ESI) (M+H)+=269.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07375101B2
Source dataset	uspto-grants-2008_05
ORD ID	ord-94315c751e8b4bf9b15ab6a8f5b6c851
Source note	uspto-grants-2008_05