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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Sodium Carbonate → (10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3,4-dihydro-naphthalen-1-yl)-3-methyl-phenyl]-methanone

HRID 1794007
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HRID 1794007 반응식
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20](B4OC(C)(C)C(C)(C)O4)=[C:19]([CH3:32])[CH:18]=3)=[O:16])[CH2:6][C:5]=12.FC(F)(F)S(O[C:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42][CH2:41][CH:40]=1)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.C(OCC)(=O)C.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:22]=[CH:21][C:20]([C:39]4[C:48]5[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=5)[CH2:42][CH2:41][CH:40]=4)=[C:19]([CH3:32])[CH:18]=3)=[O:16])[CH2:6][C:5]=12
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참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 10967830Methanesulfonic acid, trifluoro-, 3,4-dihydro-1-naphthalenyl esterHCID 22219714(10,11-Dihydro-5H-pyrrolo [2,1-c][1,4] benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone

생성물 1

HCID 9867363(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[4-(3,4-dihydro-naphthalen-1-yl)-3-methyl-phenyl]-methanone수율 90.9%

시약·촉매·용매

3
HCID 53485975CID 53485975촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

(10,11-Dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepin-10-yl)-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone of Example 2, Step B (0.760 g, 1.89 mmol), 3,4-dihydro-naphthalen-1-yl trifluoromethanesulfonate (0.579 g, 2.08 mmol) and dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (0.046 g, 0.0567 mmol) were combined in N,N-dimethylformamide (9.5 mL). 2 M aqueous sodium carbonate (4.73 mL, 9.45 mmol) was added and the reaction heated to 60° C. for 3 hours. After cooling to room temperature, the reaction mixture was diluted with ethyl acetate (100 mL) and washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated and the residue purified by flash column chromatography (silica, 30% ethyl acetate in hexanes). Recrystallization from petroleum ether afforded the title compound (0.740 g) as white crystals identical to the material of Example 31.

후처리

  1. temperatureAfter cooling to room temperature
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue purified by flash column chromatography (silica, 30% ethyl acetate in hexanes)
  7. customRecrystallization from petroleum ether

출처 및 근거

ORD 기록
ord-bbfd2716e5c346f4a8aedf6373a44fd7
출처 데이터셋
uspto-grants-2006_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07022699B2

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