Sodium Bicarbonate → 3,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridine

HRID 1987316노트

반응식

HRID 1987316 반응식
C([N:4]1[C@H:9]([C:10]2[C:15]([CH3:16])=[CH:14][CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:7][CH2:6][C@@H:5]1[C:17]1[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=1)C=C.C([O-])(O)=O.[Na+]>C(Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:16][C:15]1[C:10]([C@H:9]2[CH2:8][CH2:7][CH2:6][C@@H:5]([C:17]3[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][N:18]=3)[NH:4]2)=[N:11][CH:12]=[CH:13][CH:14]=1

참가 물질

5

반응물 2

HCID 516892Sodium BicarbonateHCID 674222901'-Allyl-3,3''-dimethyl-1',2',3',4',5',6'-hexahydro-cis-[2,2'; 6',2'']terpyridine

생성물 1

HCID 575911373,3''-Dimethyl-1',2',3',4',5', 6'-hexahydro-cis-[2,2';6',2'']terpyridine수율 85%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6344Dichloromethane용매

실험 절차

To a solution of 1′-allyl-3,3″-dimethyl-1′,2′,3′,4′,5′,6′-hexahydro-cis-[2,2′;6′,2″]terpyridine (142 mg, 0.462 mmol) in CH2Cl2 was added 1,3-dimethylbarbaturic acid (361 mg, 2.31 mmol) and Pd(PPh3)4 (53 mg, 0.046 mmol) and the reaction mixture was stirred for 20 h. Saturated solution of NaHCO3 (10 mL) was added and the mixture was extracted with CH2Cl2 (3 times 20 mL). The organic extracts were dried (MgSO4), filtered and concentrated. The crude material was purified by flash column chromatography on silica gel (9:1:0.2 CH2Cl2-MeOH—NH4OH) to provide 105 mg (85%) of the 3,3″-dimethyl-1′,2′,3′,4′,5′, 6′-hexahydro-cis-[2,2′;6′,2″]terpyridine as a clear oil. 1H NMR(CDCl3) δ 1.51-1.63 (m, 2H), 1.76-1.85 (m, 3H), 2.11-2.15 (m, 1H), 2.37 (s, 6H), 3.10-3.30 (m, 1H), 4.22 (d, 2H, J=10.8 Hz), 7.02 (dd, 2H, J=7.5, 4.5 Hz), 7.38 (d, 2H, J=7.5 Hz), 8.45 (d, 2H, J=4.5 Hz); 13C NMR (CDCl3) δ 18.68, 25.84, 32.28, 57.60, 121.96, 129.73, 138.04, 147.31, 160.94; ES-MS m/z 269.1 (M+H). Anal. Calcd. for C17H21N3.0.1CH2Cl2: C, 74.45; H, 7.75; N, 15.23. Found: C, 74.70; H, 7.80; N, 15.18.

후처리

  1. extractionthe mixture was extracted with CH2Cl2 (3 times 20 mL)
  2. dry with materialThe organic extracts were dried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash column chromatography on silica gel (9:1:0.2 CH2Cl2-MeOH—NH4OH)

출처 및 근거

ORD 기록
ord-bb81ad8e1fbd414a8c17891a7401612a
출처 데이터셋
uspto-grants-2009_06
특허 번호
US07550484B2

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