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Triethylamine → ethyl 2-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate

HRID 715288
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HRID 715288 반응식
Cl[C:2]1[C:7]2[CH2:8][N:9]([CH:12]([C:14]3[CH:15]=[N:16][C:17]([O:21][CH2:22][C:23]([F:26])([F:25])[F:24])=[C:18]([Cl:20])[CH:19]=3)[CH3:13])[C:10](=[O:11])[C:6]=2[CH:5]=[CH:4][N:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.CN([CH:66]=[O:67])C.[CH3:68][CH2:69][OH:70]>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:18]1[CH:19]=[C:14]([CH:12]([N:9]2[C:10](=[O:11])[C:6]3[CH:5]=[CH:4][N:3]=[C:2]([C:66]([O:70][CH2:69][CH3:68])=[O:67])[C:7]=3[CH2:8]2)[CH3:13])[CH:15]=[N:16][C:17]=1[O:21][CH2:22][C:23]([F:26])([F:25])[F:24]
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참가 물질

7

반응물 4

HCID 8471TriethylamineHCID 812191,3-Bis(diphenylphosphino)propaneHCID 19794673N,N-dimethylformamide ethanolHCID 898746024-chloro-2-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one

생성물 1

HCID 89874895ethyl 2-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-1-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridine-4-carboxylate
수율 73%

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 962Water용매

반응 조건

온도
100 °C

실험 절차

A mixture of 4-chloro-2-(1-(5-chloro-6-(2,2,2-trifluoroethoxy)pyridin-3-yl)ethyl)-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-1-one (200 mg, 0.49 mmol, Intermediate-9, single enantiomer), palladium(II) acetate (33 mg, 0.15 mmol, 1,3-bis(diphenylphosphino)propane (20 mg, 0.049 mmol), and triethylamine (150 mg, 1.5 mmol) in DMF/EtOH (2:1, 14 mL) is heated at 100° C. overnight under carbon monoxide atmosphere. The mixture is diluted with water, and filtered through a pad of Celite™. The Celite™ pad is washed with EtOAc/toluene (2:1) mixed solvent. The filtrate is washed with water, brine, and dried over sodium sulfate. The organic layer is filtered, and the filtrate is concentrated. The residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1 to 1:2) to give 160 mg (73% yield) of the title compound as yellow solid.

후처리

  1. filtrationfiltered through a pad of Celite™
  2. washThe Celite™ pad is washed with EtOAc/toluene (2:1)
  3. additionmixed solvent
  4. washThe filtrate is washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. filtrationThe organic layer is filtered
  7. concentrationthe filtrate is concentrated
  8. customThe residue is purified by column chromatography on silica gel eluting with n-hexane/EtOAc (1:1 to 1:2)

출처 및 근거

ORD 기록
ord-83ca7ee3a02b45c4996a372ae88089df
출처 데이터셋
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09187475B2

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