Sodium Carbonate → HCID 67050608, compound

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	Ethanamine, 2-(methylsulfonyl)-, hydrochloride (1:1)	HCID 17749886	—
Reactant	HCID 67050629	HCID 67050629	—
Catalyst	palladium(II) acetate	HCID 167845	—
Solvent	Toluene	HCID 1140	—
Product	HCID 67050608	HCID 67050608	183.6%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A suspension of 2-(3-(8-bromo-N-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamido)-4-chlorobenzamido)ethyl acetate (400 mg, 0.69 mmol), Pd(OAc)2 (10 mg, 0.045 mmol), Xantphos (40 mg, 0.069 mmol), MeSO2CH2CH2NH2.HCl (165 mg, 1.04 mmol) and Na2CO3 (219 mg, 2.07 mmol) in toluene (5 mL) was heated at 80° C. under atmosphere of CO from balloon overnight. Then it was filtrated and concentrated, the crude product was purified by column (EtOAc:MeOH=10:1) to afford 385 (76.8 mg, yield: 18%). 1HNMR (DMSO-d6, 400 MHz): δ8.70 (t, J=5.6 Hz, 1H), 8.61 (d, J=5.6 Hz, 1H), 8.07-7.41 (m, 6H), 6.57 (s, 1H), 4.72 (s, 1H), 4.71 (t, J=5.6 Hz, 1H), 3.63-2.95 (m, 16H). LC-MS: (ESI, m/z)=606 [M+H]+

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09175009B2
Source dataset	uspto-grants-2015_11
ORD ID	ord-ea29449e91d243eaad0620bd964c0b73
Source note	uspto-grants-2015_11