Diethylamine → (+/-)-2-[(4-Methylphenyl)ethynyl]-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 2262850

반응식

HRID 2262850 반응식
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][C:6]3[CH2:23][C:13]4([C:21]5[C:16](=[N:17][CH:18]=[CH:19][CH:20]=5)[NH:15][C:14]4=[O:22])[CH2:12][C:7]=3[CH:8]=2)[N:3]=1.[C:24]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)#[CH:25].C(NCC)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:32][C:29]1[CH:30]=[CH:31][C:26]([C:24]#[C:25][C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][C:6]4[CH2:23][C:13]5([C:21]6[C:16](=[N:17][CH:18]=[CH:19][CH:20]=6)[NH:15][C:14]5=[O:22])[CH2:12][C:7]=4[CH:8]=3)[N:3]=2)=[CH:27][CH:28]=1

참가 물질

6

반응물 3

HCID 8021DiethylamineHCID 13018p-EthynyltolueneHCID 59594283(+/-)-2-Chloro-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one2회

생성물 1

HCID 16736992(+/-)-2-[(4-Methylphenyl)ethynyl]-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매HCID 6228Dimethylformamide용매

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온도
120 °C

실험 절차

A stirred mixture of (±)-2-chloro-6,8-dihydrospiro[cyclopenta[g]quinoline-7,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (15 mg, 0.047 mmol, described in Intermediate 20), 4-ethynyltoluene (7 mg, 0.061 mmol), PdCl2(PPh3)2 (4 mg, 0.006 mmol), and diethylamine (0.073 mL, 0.70 mmol) in DMF (0.5 mL) was heated at 120° C. in a microwave reactor for 5 min. The cooled mixture was partitioned between saturated aqueous NaHCO3 (3 mL) and EtOAc (5 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. The product-containing fractions were combined and concentrated to give a crude product. This was further purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, to give the title compound. MS: m/z=402 (M+1). HRMS: m/z=402.1609; calculated m/z=402.1601 for C27H20N3O.

후처리

  1. customThe cooled mixture was partitioned between saturated aqueous NaHCO3 (3 mL) and EtOAc (5 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by HPLC
  6. washeluting with a gradient of H2O
  7. concentrationconcentrated
  8. customto give a crude product
  9. customThis was further purified by silica gel chromatography
  10. washeluting with a gradient of CH2Cl2

출처 및 근거

ORD 기록
ord-115d3b3c01474614915caad82e2547e1
출처 데이터셋
uspto-grants-2010_12
특허 번호
US07851464B2

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