Cesium carbonate → Methyl 2-((2,6-dimethyl-1-piperidinyl)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-4-carboxylate

HRID 1662472Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[F:21].[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[NH:24]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O>[CH3:22][CH:23]1[CH2:28][CH2:27][CH2:26][CH:25]([CH3:29])[N:24]1[CH2:2][C:3]1[CH:8]=[C:7]([C:9]([O:11][CH3:12])=[O:10])[CH:6]=[CH:5][C:4]=1[C:13]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:14]=1[F:21]

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 66.69A (0.094 g, 0.30 mmol), 2,6-dimethylpiperidine (0.069 g, 0.61 mmol) (commercially available from Aldrich) and cesium carbonate (0.20 g, 0.61 mmol) in DMSO (4 mL) was stirred at 70° C. for 24 hours. The product was purified by reverse phase HPLC to give 66.69B in 30% yield.

Workup

customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record: ord-32b1668f92044fdd9538ca2d25b3349b
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08030354B2

Reaction notes

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