p-Toluenesulfonic acid → 6-(4-Chloro-phenyl)-2-(4-pyrrolidin-1-ylmethyl-phenylethynyl)-quinoline

HRID 1916753노트

반응식

HRID 1916753 반응식
C1(C)C=CC(S(O)(=O)=O)=CC=1.[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]([C:29]#[C:30][C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[CH:23]=[CH:22]3)=[CH:15][CH:14]=1.[NH:39]1[CH2:43][CH2:42][CH2:41][CH2:40]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.O.C(O)(=O)C>[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[N:25]=[C:24]([C:29]#[C:30][C:31]2[CH:38]=[CH:37][C:34]([CH2:35][N:39]4[CH2:43][CH2:42][CH2:41][CH2:40]4)=[CH:33][CH:32]=2)[CH:23]=[CH:22]3)=[CH:15][CH:14]=1

참가 물질

9

반응물 5

HCID 6101p-Toluenesulfonic acidHCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 859696974-[6-(4-Chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde

생성물 1

HCID 598358586-(4-Chloro-phenyl)-2-(4-pyrrolidin-1-ylmethyl-phenylethynyl)-quinoline

시약·촉매·용매 3

HCID 962Water촉매HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매

실험 절차

3 mg p-toluenesulphonic acid and 100 μL glacial acetic acid are added to a solution of 290 mg (0.78 mmol) 4-[6-(4-chloro-phenyl)-quinoline-2-ylethynyl]-benzaldehyde and 56 mg (0.78 mmol) pyrrolidine in 10 mL THF at RT and stirred for 30 minutes. Then 334 mg (1.57 mmol) NaBH(OAc)3 are added batchwise and the reaction mixture is stirred for 14 h. A few drops of water are added dropwise to the reaction mixture and this is stirred for 15 minutes. The reaction mixture is then combined with K2CO3 and filtered. The filtrate is evaporated down. The purification is carried out by column chromatography on silica gel (DCM/MeOH/NH3 90:10:1).

후처리

  1. stirringthe reaction mixture is stirred for 14 h
  2. stirringthis is stirred for 15 minutes
  3. filtrationfiltered
  4. customThe filtrate is evaporated down
  5. customThe purification

출처 및 근거

ORD 기록
ord-c4b65b1e8e784d43888d5e5ac4502309
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

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