Cesium carbonate → HCID 67340638, compound

HRID 1670124Notes

Reaction equation

HRID 1670124 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)=[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(OC(=O)CCCOC1C=CC=C(CCCCCCOC2C=C(C(N3CC[C:80]([F:84])([F:83])[CH2:79]3)=O)C=C(Br)C=2)C=1CCC(OCC)=O)C.C1(B(O)O)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC.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][CH:36]=[CH:35][CH:34]=3)[CH:25]=[C:26]([C:28]([N:29]3[CH2:30][CH2:79][C:80]([F:84])([F:83])[CH2:31]3)=[O:32])[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 66827Phenylboronic AcidHCID 67337985HCID 67337985, compoundHCID 67339165HCID 67339165, compound

Product 1

HCID 67340638HCID 67340638, compoundYield 58%

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-(3,3-difluoro-pyrrolidine-1-carbonyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (135 mg, 0.194 mmol), phenylboronic acid (48.27 mg, 0.388 mmol), PdCl2(dppf) (21.24 mg, 0.03 mmol) and cesium carbonate (127.3 mg, 0.388 mmol) in 1,2-dimethoxyethane (5.0 mL) to obtain 4-[3-{6-[5-(3,3-difluoro-pyrrolidine-1-carbonyl)-biphenyl-3-yloxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (78 mg, 58%) as a colorless oil.

Sources & evidence

ORD record
ord-77fb65a18b32449289b766de09f47dfe
Source dataset
uspto-grants-2011_08
Patent number
US07989454B2

Reaction notes

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