Pyridine → HCID 86076940, compound

HRID 734862Notes

Reaction equation

HRID 734862 reaction equation
N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[CH:38][C:39]([C:42]#[C:43][C:44]3[CH:45]=[CH:46][C:47]([CH2:50][CH2:51][CH2:52][OH:53])=[N:48][CH:49]=3)=[N:40][CH:41]=2)=[CH:32][CH:31]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:37]=[CH:38][C:39]([C:42]#[C:43][C:44]3[CH:45]=[CH:46][C:47]([CH2:50][CH2:51][CH:52]=[O:53])=[N:48][CH:49]=3)=[N:40][CH:41]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 69059110HCID 69059110, compound

Product 1

HCID 86076940HCID 86076940, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.62 mL (20.07 mmol) of pyridine and 8.51 g (3.01 mmol) of Dess-Martin periodinane solution (15% in DCM) were added to a solution of 0.70 g (2.01 mmol) of 3-{5-[5-(4-chlorophenyl)pyridin-2-ylethynyl]pyridin-2-yl}propan-1-ol in 50 mL of DCM and the mixture was stirred for 16 hours at RT. Semisaturated aqueous sodium bicarbonate solution was added and the aqueous phase was extracted with MTBE. The combined organic extracts were dried over magnesium sulfate and evaporated down in vacuo. The residue was purified by HPLC-MS (Zorbax Bonus C18 amide-phase 5 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v). Yield: 115 mg (17% of theoretical); C21H15ClN2O (M=346.809); calc.: molpeak (M+H)+: 347/349 (Cl); found: molpeak (M+H)+: 347/349 (Cl); HPLC-MS: 6.70 minutes (method A).

Workup

  1. extractionthe aqueous phase was extracted with MTBE
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. customevaporated down in vacuo
  4. customThe residue was purified by HPLC-MS (Zorbax Bonus C18 amide-phase 5 μm, gradient 0.15% formic acid in water/acetonitrile 10/90→90/10 v/v)
  5. custom6.70 minutes (method A)

Sources & evidence

ORD record
ord-806086c272e54c4f9edb53334496bb5f
Source dataset
uspto-grants-2009_09
Patent number
US07592358B2

Reaction notes

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