Potassium Carbonate → Methyl 5-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-methoxybenzoate

HRID 2247433ノート

反応式

HRID 2247433 の反応式
Br[C:2]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].[CH3:19][O:20][C:21]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[CH:27][C:22]=1[C:23]([O:25][CH3:26])=[O:24].C(=O)([O-])[O-].[K+].[K+]>C(COC)OC>[C:8]([O:7][C:6]([NH:5][CH2:4][C:3]1[CH:13]=[C:14]([O:17][CH3:18])[CH:15]=[CH:16][C:2]=1[C:28]1[CH:29]=[CH:30][C:21]([O:20][CH3:19])=[C:22]([CH:27]=1)[C:23]([O:25][CH3:26])=[O:24])=[O:12])([CH3:11])([CH3:10])[CH3:9]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22930485Tert-butyl (2-bromo-5-methoxybenzyl)carbamateHCID 22930502Methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

生成物 1

HCID 59219129Methyl 5-(2-{[(t-butoxycarbonyl)amino]methyl}-4-methoxyphenyl)-2-methoxybenzoate収率 112.5%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

570 mg of t-butyl N-(2-bromo-5-methoxybenzyl)carbamate, 440 mg of methyl 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 86 mg of dichlorobistriphenyl phosphinoferrocene palladium and 1.0 g of potassium carbonate were dissolved in 15 ml of dimethoxyethane, and the mixture was heated at 80° C. for 24 hours in a nitrogen atmosphere. The reaction mixture was filtered through Celite, and the filtrate was evaporated. The residue was purified by silica gel column, to give 680 mg of the title compound in the 3:1 hexane-ethyl acetate fraction.

後処理

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate was evaporated
  3. customThe residue was purified by silica gel column

出典と根拠

ORDレコード
ord-8f219ca6433f421cab9d4cb26e076161
出典データセット
uspto-grants-2010_03
特許番号
US07687664B2

反応ノート

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