Sodium Carbonate → 1-(4-Ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)phenyl]isoquinoline

HRID 1251221노트

반응식

HRID 1251221 반응식
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](OB(O)O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[C:22]1[N:23]=[C:24]([N:32]2[CH2:37][CH2:36][N:35]([CH2:38][CH3:39])[CH2:34][CH2:33]2)[C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.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>[CH2:38]([N:35]1[CH2:34][CH2:33][N:32]([C:24]2[C:25]3[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:31]=[C:22]([C:14]3[CH:15]=[CH:16][C:11]([CH2:10][CH2:9][O:8][CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[CH:12][CH:13]=3)[N:23]=2)[CH2:37][CH2:36]1)[CH3:39]

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 225024471-(1-Ethylpiperazin-4-yl)-3-bromoisoquinolineHCID 225024564-(2-Benzyloxyethyl)phenylboric acid3회

생성물 1

HCID 177943201-(4-Ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)phenyl]isoquinoline수율 72.3%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 1140Toluene용매

실험 절차

4-(2-Benzyloxyethyl)phenylboric acid (0.40 g) and 3-bromo-1-(4-ethylpiperazin-1-yl)isoquinoline (0.65 g) were heated under reflux in the presence of tetrakistriphenylphosphinepalladium(0) (0.09 g) in toluene (50 ml) and a 10% aqueous solution of sodium carbonate (30 ml) in nitrogen atmosphere for 1 hr. To the mixture was additionally added 4-(2-benzyloxyethyl)phenylboric acid (0.40 g), and the mixture was heated under reflux for 1.5 hr. 4-(2-Benzyloxyethyl)phenylboric acid (0.40 g) was again added, and the mixture was heated under reflux overnight. The organic layer was separated, and it was extracted with 2N hydrochloric acid twice. The resulting aqueous layer was washed with ethyl acetate, adjusted to pH 10 with a 8N aqueous solution of sodium hydroxide, extracted with ethyl acetate, washed with a 10% aqueous solution of sodium carbonate and brine, and then dried over magnesium sulfate. The solvent was evaporated, and the resulting residue was purified by silica gel column chromatography (chloroform/methanol system, and then ethyl acetate/acetone system), to give 1-(4-ethylpiperazin-1-yl)-3-[4-(2-benzyloxyethyl)phenyl]isoquinoline (0.48 g) as a colorless viscous oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1.5 hr
  3. temperaturethe mixture was heated
  4. temperatureunder reflux overnight
  5. customThe organic layer was separated
  6. extractionit was extracted with 2N hydrochloric acid twice
  7. washThe resulting aqueous layer was washed with ethyl acetate
  8. extractionextracted with ethyl acetate
  9. washwashed with a 10% aqueous solution of sodium carbonate and brine
  10. dry with materialdried over magnesium sulfate
  11. customThe solvent was evaporated
  12. customthe resulting residue was purified by silica gel column chromatography (chloroform/methanol system

출처 및 근거

ORD 기록
ord-f4e3cc9f8681427e860b664dab04d645
출처 데이터셋
uspto-grants-2002_01
특허 번호
US06340759B1

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