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Potassium Carbonate → 4-(4-Fluoro-phenyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole

HRID 533725
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HRID 533725 반응식
Cl[C:2]1[C:10]2[C:9]3[CH2:11][NH:12][CH2:13][CH2:14][C:8]=3[NH:7][C:6]=2[N:5]=[CH:4][CH:3]=1.[F:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.CCOC(C)=O.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:15][C:16]1[CH:21]=[CH:20][C:19]([C:2]2[C:10]3[C:9]4[CH2:11][NH:12][CH2:13][CH2:14][C:8]=4[NH:7][C:6]=3[N:5]=[CH:4][CH:3]=2)=[CH:18][CH:17]=1
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참가 물질

8

반응물 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 666779724-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole

생성물 1

HCID 468431424-(4-Fluoro-phenyl)-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3',4'-d]pyrrole수율 29%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 218864351,4-Dioxane--water (1/1)용매HCID 22728543Water ethylacetate용매

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온도
100 °C

실험 절차

4-Chloro-6,7,8,9-tetrahydro-5H-dipyrido[2,3-b;3′,4′-d]pyrrole (100 mg, 0.48 mmol), 4-fluorophenylboronic acid (135 mg, 0.96 mmol), Pd(OAc)2 (5 mg, 0.02 mmol), S-Phos (20 mg, 0.05 mmol), and K2CO3 (266 mg, 1.93 mmol) were dissolved in dioxane/H2O (2.2 mL, 10/1, v/v), and stirred overnight at 100° C. The reaction mixture diluted with EtOAc/H2O, and filtered through an Extrelut column. The column was washed with EtOAc, and the filtrate was concentrated. The crude material was triturated with EtOAc, filtered, washed with EtOAc, and dried under vacuum to provide 6 (37 mg, 29% yield) as a tan solid. LC-MS (M+H=269, obsd.=269).

후처리

  1. filtrationfiltered through an Extrelut column
  2. washThe column was washed with EtOAc
  3. concentrationthe filtrate was concentrated
  4. customThe crude material was triturated with EtOAc
  5. filtrationfiltered
  6. washwashed with EtOAc
  7. customdried under vacuum

출처 및 근거

ORD 기록
ord-e34ebba37db2424d9cdffd525904dd65
출처 데이터셋
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08853391B2

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