Cesium carbonate → HCID 67339962, compound

HRID 1670122Notes

Reaction equation

HRID 1670122 reaction equation
[CH2:1]([O:3][C:4](=[O:48])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35](F)[CH:34]=3)[CH:25]=[C:26]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH:27]=2)[C:10]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH3:2].C([O:51]C(=O)CCCOC1C=CC=C(CCCCCCOC2C=C(C(=O)N(C)C)C=C(Br)C=2)C=1CCC(OCC)=O)C.FC1C=CC(B(O)O)=CC=1O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(COC)OC.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH2:1]([O:3][C:4](=[O:48])[CH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:23]=[C:24]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[C:35]([OH:51])[CH:34]=3)[CH:25]=[C:26]([C:28](=[O:32])[N:29]([CH3:31])[CH3:30])[CH:27]=2)[C:10]=1[CH2:41][CH2:42][C:43]([O:45][CH2:46][CH3:47])=[O:44])[CH3:2]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 44717470(4-Fluoro-3-hydroxyphenyl)boronic acidHCID 67338116HCID 67338116, compoundHCID 67339165HCID 67339165, compound

Product 1

HCID 67339962HCID 67339962, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

The title compound was prepared by the same method as 4-{3-[6-(5-dimethylcarbamoyl-3′,4′-difluoro-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester starting from 4-{3-[6-(3-bromo-5-dimethylcarbamoyl-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (150 mg, 0.236 mmol), 4-fluoro-3-hydroxyphenylboronic acid (74 mg, 0.472 mmol), PdCl2(dppf) (29 mg, 0.04 mmol) and cesium carbonate (153 mg, 0.472 mmol) in dimethoxyethane (5 mL) to obtain 4-{3-[6-(5-dimethylcarbamoyl-4′-fluoro-3′-hydroxy-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (150 mg, 95%) as a colorless oil.

Sources & evidence

ORD record
ord-b238626908e04bf8b982fd0ac91d638b
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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