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Potassium Carbonate → Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-hydroxyphenyl)-6-fluorobenzoate

HRID 2247429
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HRID 2247429 반응식
[OH:1][C:2]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13][C:3]=1[CH2:4][NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9].Br[C:27]1[CH:28]=[C:29]([C:34]([F:37])=[CH:35][CH:36]=1)[C:30]([O:32][CH3:33])=[O:31].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]([C:27]2[CH:28]=[C:29]([C:34]([F:37])=[CH:35][CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:15]=[CH:16][C:2]=1[OH:1])=[O:12])([CH3:9])([CH3:10])[CH3:11]
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참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 21525435Methyl 5-bromo-2-fluorobenzoateHCID 59219096Tert-butyl 2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzylcarbamate

생성물 1

HCID 59219269Methyl 3-(3-{[(t-butoxycarbonyl)amino]methyl}-4-hydroxyphenyl)-6-fluorobenzoate수율 72.6%

시약·촉매·용매 1

HCID 8071
1,2-Dimethoxyethane
용매

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온도
80 °C

실험 절차

501 mg of t-butyl N-[2-hydroxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]carbamate, 370 mg of methyl 3-bromo-6-fluorobenzoate, 80 mg of dichlorobistriphenyl phosphinoferrocene palladium and 500 mg of potassium carbonate were dissolved in 8 ml of dimethoxyethane and stirred overnight at 80° C. 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 391 mg of the title compound in the 4:1 hexane-ethyl acetate fraction.

후처리

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

출처 및 근거

ORD 기록
ord-4fa81894aa564085b69c9812e2870bc8
출처 데이터셋
uspto-grants-2010_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07687664B2

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