Dichloromethane → 5-Nitro-3-phenylpyridin-2-ol

HRID 41980

Reaction equation

HRID 41980 reaction equation
I[C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[C:12]1(B(O)O)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(Cl)Cl.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O>[N+:8]([C:6]1[CH:7]=[C:2]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]([OH:11])=[N:4][CH:5]=1)([O-:10])=[O:9]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10796Cesium carbonateHCID 66827Phenylboronic AcidHCID 178526840HCID 178526840, compound

Product 1

HCID 1785268355-Nitro-3-phenylpyridin-2-ol

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

In a schlenck tube, a mixture of 3-iodo-5-nitropyridin-2-ol (7.52 mmol, 2 g), phenylboronic acid (8.28 mmol, 1.01 g), PdCl2dppf.DCM (0.75 mmol, 0.6 g), Cs2CO3 (22.56 mmol, 7.4 g) in a dioxane/water 4:1 mixture (26 ml) was heated at 100° C. for 4 hours, under argon atmosphere. The solvent was evaporated and the crude mixture was extracted between water and ethyl acetate. The organic phase was evaporated and the crude was suspended in methanol affording a solid that was filtered off and dried under vacuum overnight affording 1.2 g (74% of yield) of the expected product.

Workup

  1. customThe solvent was evaporated
  2. extractionthe crude mixture was extracted between water and ethyl acetate
  3. customThe organic phase was evaporated
  4. filtrationthat was filtered off
  5. customdried under vacuum overnight
  6. customaffording

Sources & evidence

ORD record
ord-c87b15bf4ba24b01a04e01ed10774af2
Source dataset
uspto-grants-2013_09
Patent number
US08536165B2

Linked notes

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