4-Fluorophenol → HCID 21901973, compound

HRID 1160346Notes

Reaction equation

HRID 1160346 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH:30]([CH2:34]OS(C)(=O)=O)[CH2:29]3)=[O:27])[CH2:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1.O1C2C=CC(OCC3CCCN(C(C4(C5C=CC(Cl)=CC=5)CCC4)=O)C3)=CC=2OC1>>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2([C:26]([N:28]3[CH2:33][CH2:32][CH2:31][CH:30]([CH2:34][O:8][C:5]4[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=4)[CH2:29]3)=[O:27])[CH2:25][CH2:24][CH2:23]2)=[CH:18][CH:17]=1

Participants

5

Reactant 4

HCID 97324-FluorophenolHCID 10796Cesium carbonateHCID 12992442Methanesulfonic acid 1-[1-(4-chloro-phenyl)-cyclobutanecarbonyl]-piperidin-3-ylmethyl esterHCID 21902076HCID 21902076, compound

Product 1

HCID 21901973HCID 21901973, compoundYield 57.4%

Procedure

Compound 84 was synthesized from 4-fluorophenol (0.29 g, 2.60 mmol), cesium carbonate (1.27 g, 3.89 mmol) and compound 43 (1.0 g, 2.60 mmol), using the method described for the synthesis of compound 44 to give 0.60 g of the desired product 84. C23H25ClFNO2, LRMS (m/z)=402 (MH+).

Sources & evidence

ORD record
ord-82ae4c4d2f5d4154931beaf245e5f3ce
Source dataset
uspto-grants-2010_10
Patent number
US07816375B2

Reaction notes

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