Cesium carbonate → HCID 72949981, compound

HRID 517297Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][CH2:12][CH:11]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[S:10]2(=[O:22])=[O:21])=[C:4]([F:23])[CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[N:30]1([C:36](=[O:38])[CH3:37])[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[O:21]=[S:10]1(=[O:22])[CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:12][CH2:13][CH2:14][N:9]1[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([N:33]2[CH2:34][CH2:35][N:30]([C:36](=[O:38])[CH3:37])[CH2:31][CH2:32]2)=[CH:3][C:4]=1[F:23]

Participants

Conditions

Temperature: 80 °C

Procedure

2-[(4-Bromo-2-fluoro-phenyl)methyl]-6-phenyl-thiazinane 1,1-dioxide (208 mg, 0.52 mmol), Pd(OAc)2 (5.8 mg, 0.026 mmol), 2-dicyclohexylphosphine-2′,6′-di-iso-propoxy-1,1′-biphenyl (24.8 mg, 0.052 mmol) and cesium carbonate (254 mg, 0.78 mmol) were weighed out in a vial and the vial was purged with nitrogen. 1,4-Dioxane (2.5 mL) and 1-piperazin-1-ylethanone (100 mg, 0.78 mmol) were then added and the reaction was stirred at 80° C. for 2 hours. The reaction was then filtered through diatomaceous earth, concentrated and purified by reverse-phase HPLC to give 1-(4-(4-((1,1-dioxido-6-phenyl-1,2-thiazinan-2-yl)methyl)-3-fluorophenyl)piperazin-1-yl)ethanone (210 mg, 89% yield).

Workup

customwas purged with nitrogen
filtrationThe reaction was then filtered through diatomaceous earth
concentrationconcentrated
custompurified by reverse-phase HPLC

Sources & evidence

ORD record: ord-2b7aef97d1af45d1b421efa083354ca8
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115101B2

Reaction notes

Loading…