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Ethyl Acetate → (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

HRID 554621
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HRID 554621 반응식
[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10](Br)[CH:11]=1)[CH3:2].[CH2:15]([N:17]([CH2:23][C:24]1[CH:29]=[C:28]([C:30]([F:33])([F:32])[F:31])[CH:27]=[CH:26][C:25]=1B1OC(C)(C)C(C)(C)O1)[C:18]([CH:20]1[CH2:22][CH2:21]1)=[O:19])[CH3:16].C(=O)([O-])[O-].[K+].[K+].CCOC(C)=O>COCCOC.[Cl-].[Na+].O.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.O>[CH2:1]([O:3][C:4](=[O:14])[CH2:5][C:6]1[CH:7]=[N:8][C:9]([Cl:13])=[C:10]([C:25]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[CH:29][C:24]=2[CH2:23][N:17]([C:18]([CH:20]2[CH2:22][CH2:21]2)=[O:19])[CH2:15][CH3:16])[CH:11]=1)[CH3:2]
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참가 물질

9

반응물 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58565131HCID 58565131, 화합물HCID 66607375Cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide

생성물 1

HCID 86640538(6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 57417360Sodium chloride; water용매

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온도
85 °C

실험 절차

(5-Bromo-6-chloro-pyridin-3-yl)-acetic acid ethyl ester (0.549 g, 1.97 mmol), cyclopropanecarboxylic acid ethyl-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-5-trifluoromethyl-benzyl]-amide (0.787 g, 1.97 mmol), and potassium carbonate (0.824 g, 5.91 mmol) were combined in DME (6 mL) and H2O (3 mL), and the solution was purged with N2 for 40 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.338 g, 0.20 mmol) was added, and the reaction was stirred at 85° C. for 2 hours. After cooling to room temperature, the mixture was worked-up with EtOAc, H2O, and brine, and the organic layer was separated, dried, filtered, and concentrated. The residue was purified by silica gel chromatography (0-100% EtOAc in hexanes) to give (6-chloro-5-{2-[(N-cyclopropanecarbonyl-N-ethyl-amino)-methyl]-4-trifluoromethyl-phenyl}-pyridin-3-yl)-acetic acid ethyl ester.

후처리

  1. customH2O (3 mL), and the solution was purged with N2 for 40 minutes
  2. temperatureAfter cooling to room temperature
  3. customthe organic layer was separated
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography (0-100% EtOAc in hexanes)

출처 및 근거

ORD 기록
ord-0033d9b8852848f6969734e31e3cbacd
출처 데이터셋
uspto-grants-2011_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08049015B2

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