Acetamide → HCID 68754025, compound

HRID 624274Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2([NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH2:11][O:10][CH2:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:25]([NH2:28])(=[O:27])[CH3:26].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd]>[CH3:16][C:15]([CH3:18])([S:13]([NH:12][C:8]1([C:5]2[CH:6]=[CH:7][C:2]([NH:28][C:25](=[O:27])[CH3:26])=[CH:3][CH:4]=2)[CH2:11][O:10][CH2:9]1)=[O:14])[CH3:17]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 5 mL microwave tube was added N-(3-(4-bromophenyl)oxetan-3-yl)-2-methylpropane-2-sulfinamide (436 mg, 1.312 mmol), cesium carbonate (1283 mg, 3.94 mmol), and acetamide (116 mg, 1.968 mmol) in dioxane (6.5 ml). Xantphos (76 mg, 0.131 mmol) and tris(dibenzylideneacetone)dipalladium(O) (60.1 mg, 0.066 mmol) were added; the tube was flushed with nitrogen and capped. The mixture was heated at 100° C. for 45 minutes. Aqueous work up with dichloromethane extraction gave an organic layer that was dried with sodium sulfate, filtered and concentrated under vacuum. Regular phase chromatography provided the title compound.

Workup

customthe tube was flushed with nitrogen
customcapped
extractionAqueous work up with dichloromethane extraction
customgave an organic layer that
dry with materialwas dried with sodium sulfate
filtrationfiltered
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-f0ebd671bb4548dc862a3381dcac8177
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302989B2

Reaction notes

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