Pyridine → HCID 86675604, compound

HRID 1519227Notes

Reaction equation

HRID 1519227 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH2:21][OH:22])=[N:6][CH:7]=1.N1C=CC=CC=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8][C:9]2[O:13][C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)=[N:11][C:10]=2[CH:21]=[O:22])=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 159087TriacetoxyperiodinaneHCID 71184222HCID 71184222, compound2×

Product 1

HCID 86675604HCID 86675604, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of {5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methanol (intermediate B1.1, 0.10 g, 0.30 mmol) in 5.5 ml of DCM was added pyridine (0.24 ml, 2.97 mmol), followed by Dess-Martin periodinane (0.166 g, 0.39 mmol). The reaction was allowed to proceed at rt for 2 h and quenched by the adding of 1M aq. sodium thiosulfate (5 ml) and satd. NaHCO3 (5 ml). After stirring vigorously, the reaction was diluted with water and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4 and concentrated to yield 105 mg of 5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazole-4-carbaldehyde. The aldehyde was used without further purification. LCMS [M+H]+=335.3.

Workup

  1. customquenched by the
  2. additionadding of 1M aq. sodium thiosulfate (5 ml)
  3. additionthe reaction was diluted with water
  4. extractionextracted with EtOAc
  5. washThe combined organics were washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ef5e017214e04a2f90f14bcc5c8ed3f7
Source dataset
uspto-grants-2015_07
Patent number
US09073879B2

Reaction notes

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