N,N-Diethyl-2-propanamine → [3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-4-nitro-phenyl)-methanone

HRID 1820891

반응식

HRID 1820891 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C(N(C(C)C)CC)C.[CH2:28]([O:30][C:31]1[CH:39]=[C:38]([N+:40]([O-:42])=[O:41])[CH:37]=[CH:36][C:32]=1[C:33](O)=[O:34])[CH3:29].F[P-](F)(F)(F)(F)F.Br[P+](N1CCCC1)(N1CCCC1)N1CCCC1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([C:33]([C:32]3[CH:36]=[CH:37][C:38]([N+:40]([O-:42])=[O:41])=[CH:39][C:31]=3[O:30][CH2:28][CH3:29])=[O:34])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

참가 물질

6

반응물 4

HCID 521913N,N-Diethyl-2-propanamineHCID 2733179PyBroPHCID 27363472-Ethoxy-4-nitrobenzoic acidHCID 116732853-(3,4-dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 57891702[3-(3,4-Dimethoxy-phenyl)-pyrrolo[2,3-b]pyridin-1-yl]-(2-ethoxy-4-nitro-phenyl)-methanone수율 77.5%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3-(3,4-Dimethoxy-phenyl)-1H-pyrrolo[2,3-b]pyridine 1(250 mg, 0.98 mmole) was dissolved in 50 mL of CH2Cl2. N,N-diethylisopropylamine (205 uL, 1.2 mmol), 2-ethoxy-4-nitro-benzoic acid (228 mg, 1.1 mmol) and bromotris(pyrolodino)phoshonium hexafluorophosphate (550 mg, 1.1 mmol) were added to the stirring reaction mixture. The mixture was stirred at ambient temperature for 4 h and washed consecutively with saturated sodium bicarbonate and saturated potassium bisulfate solution. The resulting solution was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% ethyl acetate in hexanes) to yield 340 mg (77%) of the titled compound as a yellow solid. MS(ESI) [M+H+]+=448.2.

후처리

  1. washwashed consecutively with saturated sodium bicarbonate and saturated potassium bisulfate solution
  2. dry with materialThe resulting solution was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (30% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-3a8ccfd22a4e4c6b98e6fdbdda52c2a2
출처 데이터셋
uspto-grants-2009_10
특허 번호
US07605168B2

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