Pyrrolidine → 5-(4-Chloro-phenyl)-2-[3-methyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

HRID 1916703Notes

Reaction equation

HRID 1916703 reaction equation
CS(O[CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:19][N:18]=2)=[CH:11][C:10]=1[CH3:30])(=O)=O.[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([C:20]2[CH:21]=[CH:22][C:17]([C:16]#[C:15][C:12]3[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[C:10]([CH3:30])[CH:11]=3)=[N:18][CH:19]=2)=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 31268PyrrolidineHCID 865946832-{4-[5-(4-Chlorophenyl)pyridin-2-ylethynyl]-2-methylphenoxy}ethyl methanesulfonate

Product 1

HCID 598357455-(4-Chloro-phenyl)-2-[3-methyl-4-(2-pyrrolidin-1-yl-ethoxy)-phenylethynyl]-pyridine

Procedure

A solution of 110 mg (0.25 mmol) 2-{4-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-2-methyl-phenoxy}-ethyl methanesulphonate in 2.11 mL (25 mmol) pyrrolidine is heated to 70° C. for 3 h. The mixture is evaporated down i. vac., the residue is combined with water, extracted exhaustively with DCM and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated and after recrystallisation from EtOH the desired product is obtained.

Workup

  1. customThe mixture is evaporated down i
  2. extractionextracted exhaustively with DCM
  3. dry with materialthe organic phase is dried over Na2SO4
  4. customafter recrystallisation from EtOH the desired product
  5. customis obtained

Sources & evidence

ORD record
ord-b77e833540484f57979a40fb72a67dd2
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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