Cesium carbonate → HCID 57863028, compound

HRID 418130Notes

Reaction equation

HRID 418130 reaction equation
[CH2:1]([O:3][C:4](=[O:42])[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]([S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])[CH:25]=[C:24](Br)[CH:23]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2].[C:43](=[O:46])([O-])[O-:44].[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:42])[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]([S:28]([CH:31]([CH3:33])[CH3:32])(=[O:30])=[O:29])[CH:25]=[C:24]([C:9]3[CH:14]=[CH:13][C:12]4[O:44][CH2:43][O:46][C:11]=4[CH:10]=3)[CH:23]=2)[C:10]=1[CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH3:2]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 57863063HCID 57863063, compound

Product 1

HCID 57863028HCID 57863028, compoundYield 159.1%

Reagents, catalysts & solvents 1

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

Procedure

A similar procedure as described in Example 41, step 1 was used, starting from 4-[3-{6-[3-bromo-5-(propane-2-sulfony)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (175 mg, 0.26 mmol), 3,4-(methylenedioxyphenyl)boronic acid (86.6 mg, 0.52 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (28.7 mg, 0.039 mmol), and cesium carbonate (171.8 mg, 0.52 mmol) to afford 4-[3-{6-[3-benzo[1,3]dioxol-5-yl-5-(propane-2-sulfonyl)-phenoxy]-hexyl}-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (147 mg, 79%) as a colorless viscous oil: ES(+)-HRMS m/e calcd for C39H50O10S (M+Na)+ 733.3017, found 733.3017.

Sources & evidence

ORD record
ord-b43d2885819d46858d858ea99a5051a0
Source dataset
uspto-grants-2012_01
Patent number
US08093253B2

Reaction notes

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