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Potassium Carbonate → 6-(2'-Formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester

HRID 860833
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인쇄 미리보기

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HRID 860833 반응식
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18](I)=[CH:17][CH:16]=3)[C:10](=[O:22])[C:9]=2[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2].[CH:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][C:34]=1B(O)O)=[O:32].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]3[CH:20]=[CH:19][C:18]([C:34]4[CH:35]=[CH:36][CH:37]=[CH:38][C:33]=4[CH:31]=[O:32])=[CH:17][CH:16]=3)[C:10](=[O:22])[C:9]=2[N:8]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[N:7]=1)=[O:5])[CH3:2]
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참가 물질

8

반응물 3

HCID 11430Potassium CarbonateHCID 2921892-Formylphenylboronic acidHCID 22240493Ethyl 6-(4-iodophenyl)-1-(4-methoxyphenyl)-7-oxo-4,5-dihydropyrazolo[3,4-c]pyridine-3-carboxylate

생성물 1

HCID 223185346-(2'-Formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester수율 84%

시약·촉매·용매 4

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매
HCID 962Water용매2회
HCID 1140Toluene용매

실험 절차

Method A. A suspension 1-(4-methoxy-phenyl)-6-(4-iodo-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (55, 2.0 g, 3.87 mmol), 2-formylphenylboronic acid (13, 870 mg, 5.81 mmol, 1.5 equiv), and K2CO3 (1.60 g, 11.6 mmol, 3.0 equiv) in toluene (18 mL), ethanol (6 mL) and H2O (6 mL) at room temperature was degassed three times under a steady nitrogen stream before being treated with Pd(PPh3)4 (22 mg, 0.02 mmol, 5% equiv) at room temperature under N2. The reaction mixture was subsequently degassed three times again before being warmed to reflux for 12 h. When HPLC showed the Suzuki coupling reaction was complete, the reaction mixture was cooled down to 5–10° C. before being treated with water (20 mL) at 5–10° C. with good stirring. The mixture was stirred for an additional 1 h at 5–10° C. before the solids were collected by filtration. The wet cake was then thoroughly washed with water (2×30 mL) and 30% EtOAc/hexane (2×20 mL), dried in vacuo at 40–45° C. for 12 h to afford the crude desired 6-(2′-formyl-biphenyl-4-yl)-1-(4-methoxy-phenyl)-7-oxo-4,5,6,7-tetrahydro-1H-pyrazolo[3,4-c]pyridine-3-carboxylic acid ethyl ester (56, 1.61 g, 1.915 g theoretical, 84%) as off-white solids, which was found to be pure enough to do the following reaction without further purification. For 56, CIMS m/z 496 (M++H, C29H25N3O5).

후처리

  1. customThe reaction mixture was subsequently degassed three times again
  2. temperaturebefore being warmed
  3. temperatureto reflux for 12 h
  4. customthe Suzuki coupling reaction
  5. temperaturethe reaction mixture was cooled down to 5–10° C.
  6. filtrationwere collected by filtration
  7. washThe wet cake was then thoroughly washed with water (2×30 mL) and 30% EtOAc/hexane (2×20 mL)
  8. customdried in vacuo at 40–45° C. for 12 h

출처 및 근거

ORD 기록
ord-e81f14f4846d47f79cfc60c7ccc899ce
출처 데이터셋
uspto-grants-2006_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07153960B2

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