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

HRID 1916753Notes

Reaction equation

HRID 1916753 reaction equation
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

Participants

9

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterCatalystHCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-c4b65b1e8e784d43888d5e5ac4502309
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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