Pyridine → HCID 67365019, compound

HRID 271715Notes

Reaction equation

HRID 271715 reaction equation
N1C=CC=CC=1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH2:32][CH2:31][C@@H:30]([OH:33])[CH2:29]4)=[N:26][CH:27]=3)=[N:18][CH:19]=2)=[CH:10][CH:9]=1.C([O-])(O)=O.[Na+].C(OC)(C)(C)C>C(Cl)Cl>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]([C:20]#[C:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[CH2:32][CH2:31][C:30](=[O:33])[CH2:29]4)=[N:26][CH:27]=3)=[N:18][CH:19]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 15413tert-Butyl methyl etherHCID 516892Sodium BicarbonateHCID 67363290HCID 67363290, compound

Product 1

HCID 67365019HCID 67365019, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

0.43 mL (5.32 mmol) pyridine and 2.26 g (0.80 mmol, 15 percent by weight) Dess-Martin-periodinane in DCM are added to a solution of 200 mg (0.53 mmol) (R)-1-{5-[5-(4-chloro-phenyl)-pyridin-2-ylethynyl]-pyridin-2-yl}-pyrrolidin-3-ol in 10 mL DCM. The reaction mixture is stirred for 3 h at RT and added to a solution of semisaturated NaHCO3 solution and tert-butylmethylether. The aqueous phase is extracted twice with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac. The product is further reacted without purification.

Workup

  1. extractionThe aqueous phase is extracted twice with EtOAc
  2. dry with materialThe organic phase is dried over MgSO4
  3. customThe product is further reacted without purification

Sources & evidence

ORD record
ord-f5abff15a04140be826b4f963c10527c
Source dataset
uspto-grants-2008_11
Patent number
US07452911B2

Reaction notes

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