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Cesium carbonate → HCID 59496827, compound

HRID 417017
Notes
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Reaction equation

HRID 417017 reaction equation
[CH2:1]([O:3][C:4](=[O:44])[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:27]=[C:26](Br)[CH:25]=[C:24]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:23]=2)[C:10]=1[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH3:2].[C:45]1(B(O)O)[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>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:44])[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:27]=[C:26]([C:45]3[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=3)[CH:25]=[C:24]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:23]=2)[C:10]=1[CH2:37][CH2:38][C:39]([O:41][CH2:42][CH3:43])=[O:40])[CH3:2]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 59496817HCID 59496817, compound

Product 1

HCID 59496827HCID 59496827, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst

Procedure

A similar procedure as described in Example 43, step 4 was used, starting from 4-[3-[6-(3-benzyloxy-5-bromo-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (260 mg, 0.39 mmol), phenylboronic acid (95 mg, 0.78 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (73 mg, 0.1 mmol), and cesium carbonate (253 mg, 0.78 mmol) to obtain 4-[3-[6-(5-benzyloxy-biphenyl-3-yloxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (230 mg, 89%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C42H50O7 (M+Na)+ 689.3449. found 689.3447.

Sources & evidence

ORD record
ord-0c3bfdf931894962b519ab4bd37b8dd4
Source dataset
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08088936B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes