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Diisopropylethylamine → 8-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenylsulfanyl]-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

HRID 2075667
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HRID 2075667 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]3[C:10](=[CH:11][C:12](I)=[CH:13][CH:14]=3)[N:9]2[CH:25]=1)=[O:5])[CH3:2].[SH:26][C:27]1[CH:28]=[C:29]([C:33]2([C:39]#[N:40])[CH2:38][CH2:37][O:36][CH2:35][CH2:34]2)[CH:30]=[CH:31][CH:32]=1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.CCN(C(C)C)C(C)C>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]2[CH:17]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:15]3[C:10](=[CH:11][C:12]([S:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([C:33]5([C:39]#[N:40])[CH2:34][CH2:35][O:36][CH2:37][CH2:38]5)[CH:28]=4)=[CH:13][CH:14]=3)[N:9]2[CH:25]=1)=[O:5])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 187863864-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrileHCID 670906998-Iodo-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

생성물 1

HCID 248758648-[3-(4-Cyano-tetrahydro-pyran-4-yl)-phenylsulfanyl]-5-phenyl-imidazo[1,2-a]quinoline-2-carboxylic acid ethyl ester

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

1v (262 mg, 0.59 mmol), 4-(3-Mercapto-phenyl)-tetrahydro-pyran-4-carbonitrile (1w, 130 mg, 0.59 mmol), Pd2dba3 (14 mg, 0.01 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (17 mg, 0.03 mmol), and iPr2NEt (0.27 mL, 1.9 mmol) were dissolved in 1,4-dioxane (2 mL) and degassed with N2 for 10 minutes. The mixture was heated at 60° C. for 2 hours, then cooled to room temperature and concentrated. The residue was purified by silica gel chromatography to give the desired product, 1z.

후처리

  1. customdegassed with N2 for 10 minutes
  2. temperaturecooled to room temperature
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-91b7fc21fba743de9f3d9aa1dc9bf72c
출처 데이터셋
uspto-grants-2011_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07919621B2

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