Cesium carbonate → HCID 57889267, compound

HRID 1820223Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:30]=[CH:31][CH:32]=1)[C:5]([NH:7][C@H:8]([CH:27]([CH3:29])[CH3:28])[C:9]([N:11]1[CH2:16][CH2:15][C@@:14]([C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=2)([OH:17])[C:13]([CH3:26])([CH3:25])[CH2:12]1)=[O:10])=[O:6].[CH3:33][O:34][C:35]([C:37]1[CH:42]=[CH:41][C:40](B(O)O)=[CH:39][CH:38]=1)=[O:36].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([C@@:14]2([OH:17])[CH2:15][CH2:16][N:11]([C:9](=[O:10])[C@H:8]([NH:7][C:5]([C:4]3[CH:3]=[C:2]([C:40]4[CH:41]=[CH:42][C:37]([C:35]([O:34][CH3:33])=[O:36])=[CH:38][CH:39]=4)[CH:32]=[CH:31][CH:30]=3)=[O:6])[CH:27]([CH3:29])[CH3:28])[CH2:12][C:13]2([CH3:26])[CH3:25])=[CH:19][CH:20]=1

Participants

Conditions

Temperature: 60 °C

Procedure

3-Bromo-N—((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-yl)benzamide (50 mg, 0.096 mmol), 4-(methoxycarbonyl)phenylboronic acid (17 mg, 0.096 mmol), 1.5M cesium carbonate (0.192 ml, 0.287 mmol) and palladium(II) acetate (1.08 mg, 4.79 μmol) were dissolved in DMF (3 mL) in a microwave tube at 25° C. then heated at 60° C. for 30 minutes. The reaction was diluted with EtOAc then washed with water (4×). The organic layer was dried (sodium sulfate) and concentrated in vacuo to give methyl 3′-((R)-1-((S)-4-(4-chlorophenyl)-4-hydroxy-3,3-dimethylpiperidin-1-yl)-3-methyl-1-oxobutan-2-ylcarbamoyl)biphenyl-4-carboxylate (44 mg, 0.076 mmol, 80% yield) as a white solid. MS found: (M+H)+=577.32.

Workup

washthen washed with water (4×)
dry with materialThe organic layer was dried (sodium sulfate)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-d57b35dfae97448086ec1560c315eaca
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07601844B2

Reaction notes

Loading…