Cesium carbonate → HCID 67125463, compound

HRID 1470724Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].[C:7]([O:11][C:12](=[O:28])[NH:13][C@H:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1)[CH3:15])([CH3:10])([CH3:9])[CH3:8].Br[C:30]1[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:7]([O:11][C:12](=[O:28])[NH:13][C@H:14]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]2[CH2:27][CH2:26][N:25]([C:30]3[CH:35]=[CH:34][C:33]([O:36][CH2:37][CH3:38])=[CH:32][CH:31]=3)[CH2:24][CH2:23]2)=[CH:20][CH:21]=1)[CH3:15])([CH3:8])([CH3:9])[CH3:10]

Participants

Conditions

Temperature: 120 °C

Procedure

6.21 g (19.1 mmol) cesium carbonate are added to a mixture of 5.80 mg (19.1 mmol) (S)-[1-(4-piperidin-4-yl-phenyl)-ethyl]-carbamic acid tert-butyl ester (V.5), 4.21 g (21.0 mmol) 1-bromo-4-ethoxy-benzene, 454 mg (0.953 mmol) X-Phos and 214 mg (0.953 mmol) palladium(II) acetate in 50 mL toluene/10 mL tert-butanol. The mixture is stirred for 3 h at 120° C. under inert gas atmosphere. After that time, the mixture is poured into water and extracted with ethyl acetate. The organic layer is washed with water and dried over magnesium sulphate. The solvent is removed in vacuo and the residue is recrystallized from acetonitrile.

Workup

extractionextracted with ethyl acetate
washThe organic layer is washed with water
dry with materialdried over magnesium sulphate
customThe solvent is removed in vacuo
customthe residue is recrystallized from acetonitrile

Sources & evidence

ORD record: ord-d8ac133a30da4d069ab76e8ee91dabd0
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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