Water → HCID 86716131, 화합물

HRID 627560노트

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HRID 627560 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:16]2[CH:17]=[C:18]3[C:23](=[CH:24][CH:25]=2)[N:22]=[C:21](Cl)[C:20]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[C:19]3[Cl:33])([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[OH:9])=[CH:4][CH:3]=1.CC1(C)C(C)(C)OB([C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)O1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:33][C:19]1[C:18]2[C:23](=[CH:24][CH:25]=[C:16]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=3)([C:10]3[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=3)[OH:9])[CH:17]=2)[N:22]=[C:21]([C:42]2[CH:43]=[N:44][CH:45]=[CH:46][CH:47]=2)[C:20]=1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 74222811HCID 74222811, 화합물

생성물 1

HCID 86716131HCID 86716131, 화합물

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

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온도
70 °C

실험 절차

A mixture of (4-chlorophenyl)(2,4-dichloro-3-phenylquinolin-6-yl)(pyridin-3-yl)methanol (75 mg, 0.15 mmol, Example 17), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (37 mg, 0.18 mmol), PdCl2(dppf) (11 mg, 0.015 mmol) and K2CO3 (42 mg, 0.30 mmol) in 10 mL of dioxane was combined with 2 mL of water and heated to 70° C. After 3 hours, the reaction mixture was cooled to room temperature, diluted with EtOAc, and washed with water. The organic phase was dried over Na2SO4, filtered and concentrated. The residue was purified on an ISCO using 0-10% methanol in ethyl acetate and lyophilized to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3) δ=8.60 (s, 1H), 8.55 (d, J=4.0 Hz, 1H), 8.45 (d, J=3.5 Hz, 1H), 8.27-8.34 (m, 2H), 8.15 (d, J=8.6 Hz, 1H), 7.73 (dd, J=8.6, 2.0 Hz, 2H), 7.58 (d, J=7.6 Hz, 1H), 7.28-7.36 (m, 8H), 7.08-7.16 (m, 3H); MS m/e 534.8 [M+H]+.

후처리

  1. temperaturethe reaction mixture was cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic phase was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified on an ISCO

출처 및 근거

ORD 기록
ord-e635dcc392104d528fac0c267f342e05
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309222B2

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