Pyridine → HCID 86621676, 화합물

HRID 1364117노트

반응식

HRID 1364117 반응식
[N:1]1[NH:2][CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=12.[Br:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:18][C:19]1[N:24]=[CH:23][C:22]([N:2]2[CH:3]=[C:4]3[C:5]([CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]3)=[N:1]2)=[CH:21][CH:20]=1

참가 물질

6

반응물 3

HCID 1049PyridineHCID 27627062-Bromopyridine-5-boronic acidHCID 178451637HCID 178451637, 화합물

생성물 1

HCID 86621676HCID 86621676, 화합물

시약·촉매·용매 2

HCID 8895Cupric acetate촉매HCID 6344Dichloromethane용매

실험 절차

A mixture of 1,1-dimethylethyl 4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 9) (207 mg, 0.87 mmol), (6-bromo-3-pyridinyl)boronic acid (204 mg, 1.74 mmol), copper acetate (472 mg, 2.61 mmol), pyridine (140 μl, 1.74 mmol) and molecular sieves (4 Å, 750 mg) in dichloromethane (10 ml) was stirred open to the atmosphere for 8 days. Crude mixture was then filtered through a pad of celite and washed with dichloromethane and ammonia. After evaporation in vacuo, the residue was purified by SCX cartridge eluting with methanol first then 2M ammonia in methanol. The methanol fractions containing the product were combined and evaporated in vacuo. The residue was then purified by column chromatography on silica gel eluting with a mixture of hexane in ethyl acetate (10:1 to 1:1) to afford the title compound (D17). MS (ES+) m/e 393 and 395 [M+H]+.

후처리

  1. filtrationCrude mixture was then filtered through a pad of celite
  2. washwashed with dichloromethane and ammonia
  3. customAfter evaporation in vacuo
  4. customthe residue was purified by SCX cartridge
  5. washeluting with methanol first
  6. additionThe methanol fractions containing the product
  7. customevaporated in vacuo
  8. customThe residue was then purified by column chromatography on silica gel eluting with a mixture of hexane in ethyl acetate (10:1 to 1:1)

출처 및 근거

ORD 기록
ord-7f029a5836eb492894b9407909383a87
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888347B2

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