Dichloromethane → 3-[7-(2-Methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-N,N-dimethyl-benzamide

HRID 272051

반응식

HRID 272051 반응식
Br[C:2]1[N:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[CH:9][N:8](S(C3C=CC(C)=CC=3)(=O)=O)[C:5]2=[N:6][CH:7]=1.[CH3:29][N:30]([CH3:42])[C:31]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)=[O:32].C(=O)(O)[O-].[Na+].ClCCl>C(#N)C.CCOC(C)=O.Cl[Pd-2](Cl)(P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CO>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:37]3[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=3)[C:31]([N:30]([CH3:42])[CH3:29])=[O:32])[N:3]=2)[NH:8][CH:9]=1

참가 물질

9

반응물 4

HCID 6344DichloromethaneHCID 516892Sodium Bicarbonate2회HCID 27733923-(Dimethylcarbamoyl)benzeneboronic acidHCID 598360452-Bromo-7-(2-methoxy-phenyl)-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine

생성물 1

HCID 598361763-[7-(2-Methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-N,N-dimethyl-benzamide수율 54%

시약·촉매·용매 4

HCID 178418903HCID 178418903, 화합물촉매HCID 887Methanol용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 2-Bromo-7-(2-methoxy-phenyl)-5-(toluene-4-sulfonyl)-5H-pyrrolo[2,3-b]pyrazine (30 mg, 0.065 mmol), 3-dimethylaminocarbonylphenyl boronic acid (25.3 mg, 0.130 mmol) and dichlorobis(triphenylphosphino)palladium(II) (2.5 mg, 0.003 mmol) in acetonitrile (1 mL) and aqueous solution of sodium bicarbonate (2M, 1 mL) was irradiated in a Personal Chemistry Optimizer at 90° C. for 15 minutes. The crude reaction mixture was distributed between dichloromethane and a saturated aqueous solution of sodium bicarbonate. The aqueous phase was then extracted with dichloromethane and the combined organic phases were dried over sodium sulfate, filtered and concentrated. The crude brown residue was then dissolved in MeOH (5 mL), 5N KOH (50 μL) and the mixture was stirred at room temperature for 75 minutes. Removal of the solvents resulted in a yellow residue, which was then purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes, then 10% MeOH in EtOAc to afford 3-[7-(2-Methoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-N,N-dimethyl-benzamide (13.0 mg, 54% yield) as a pale yellow solid. 1H-NMR (500 MHz, CD3OD) δ8.89 (m, 1H), 8.80 (m, 1H), 8.40 (m, 1H), 8.25 (m, 2H), 7.62 (m, 1H), 7.50 (m, 1H), 7.25 (m, 1H), 7.10 (m, 2H), 3.97 (m, 3H), 3.17 (m, 3H), 3.10 (m, 3H).

후처리

  1. customwas irradiated in a Personal Chemistry Optimizer at 90° C. for 15 minutes
  2. customThe crude reaction mixture
  3. extractionThe aqueous phase was then extracted with dichloromethane
  4. dry with materialthe combined organic phases were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. dissolutionThe crude brown residue was then dissolved in MeOH (5 mL)
  8. customRemoval of the solvents
  9. customresulted in a yellow residue, which
  10. customwas then purified by flash silica gel chromatography

출처 및 근거

ORD 기록
ord-a373f472ac0d4013bb620908bdcd7431
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452993B2

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