Pyridine → HCID 67365019, compound

HRID 1916686Notes

Reaction equation

HRID 1916686 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-672889fdcf564133b011bd2a53d16aa9
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

Loading…