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Potassium Carbonate → (5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554592
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HRID 554592 반응식
[CH2:1]([N:8]([CH2:14][C:15]1[CH:20]=[C:19]([C:21]#[N:22])[CH:18]=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1)[C:9]([CH:11]1[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:32]([O:34][C:35](=[O:44])[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41](Br)[CH:42]=1)[CH3:33].C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:32]([O:34][C:35](=[O:44])[CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[C:41]([C:16]2[CH:17]=[CH:18][C:19]([C:21]#[N:22])=[CH:20][C:15]=2[CH2:14][N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:9]([CH:11]2[CH2:12][CH2:13]2)=[O:10])[CH:42]=1)[CH3:33]
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참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 54116619Ethyl 2-(5-bromopyridin-3-yl)acetateHCID 67212390Cyclopropanecarboxylic acid benzyl-[5-cyano-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amide

생성물 1

HCID 67212964(5-{2-[(Benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 313Hydrochloric Acid용매
HCID 962Water용매
HCID 80711,2-Dimethoxyethane용매

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온도
70 °C

실험 절차

Cyclopropanecarboxylic acid benzyl-[5-cyano-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzyl]-amide (1.33 g, 3.2 mmol), (5-bromo-pyridin-3-yl)-acetic acid ethyl ester (1.02 g, 4.2 mmol), and potassium carbonate (1.55 g, 11.2 mmol) were combined in DME (40 mL) and H2O (30 mL), and the solution was purged with N2 for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.370 g, 0.35 mmol) was added, and the reaction was stirred at 70° C. for 1 hour. The mixture was diluted with H2O and 1N aqueous HCl (15 mL), and extracted with EtOAc. The combined organic layers were concentrated and purified by preparative HPLC to give (5-{2-[(benzyl-cyclopropanecarbonyl-amino)-methyl]-4-cyano-phenyl}-pyridin-3-yl)-acetic acid ethyl ester, as well as the some of the hydrolyzed ester product.

후처리

  1. customH2O (30 mL), and the solution was purged with N2 for 15 minutes
  2. extractionextracted with EtOAc
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-bb027aabd8bb46da8616333f5d0354e0
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049015B2

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