(2H-1,3-benzodioxol-5-yl)boronic acid → 4-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-nitro-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester

HRID 420386Notes

Reaction equation

HRID 420386 reaction equation
[CH2:1]([O:3][C:4](=[O:39])[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]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24](I)[CH:23]=2)[C:10]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:2].[O:40]1[C:44]2[CH:45]=[CH:46][C:47](B(O)O)=[CH:48][C:43]=2[O:42][CH2:41]1>>[CH2:1]([O:3][C:4](=[O:39])[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]([N+:28]([O-:30])=[O:29])[CH:25]=[C:24]([C:47]3[CH:46]=[CH:45][C:44]4[O:40][CH2:41][O:42][C:43]=4[CH:48]=3)[CH:23]=2)[C:10]=1[CH2:32][CH2:33][C:34]([O:36][CH2:37][CH3:38])=[O:35])[CH3:2]

Participants

3

Reactant 2

HCID 2734371(2H-1,3-benzodioxol-5-yl)boronic acidHCID 575864524-{2-(2-Ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-nitro-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester

Product 1

HCID 575864714-{3-[6-(3-Benzo[1,3]dioxol-5-yl-5-nitro-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl esterYield 73.4%

Procedure

A similar procedure as described in Example 12, step 8 was used, starting from 4-{2-(2-ethoxycarbonyl-ethyl)-3-[6-(3-iodo-5-nitro-phenoxy)-hexyl]-phenoxy}-butyric acid ethyl ester (6.6 g, 10.07 mmol) and benzo[1,3]dioxol-5-yl-boronic acid (3.45 g, 20.14 mmol) to afford 4-{3-[6-(3-benzo[1,3]dioxol-5-yl-5-nitro-phenoxy)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy}-butyric acid ethyl ester (4.8 g, 73%) as a light yellow oil: EI(+)-HRMS m/e calculated for C36H43NO10 (M+Na)+ 672.2779, found 672.2773.

Sources & evidence

ORD record
ord-49b89521584a4d3ca7a46c723b7179d2
Source dataset
uspto-grants-2012_01
Patent number
US08093385B2

Reaction notes

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