3-Hydroxypyridine → HCID 58337714, compound

HRID 1887443Notes

Reaction equation

HRID 1887443 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[CH:5]=[C:4]([Cl:9])[CH:3]=1.[OH:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([Cl:9])[CH:3]=1)[O:10][C:11]1[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 27362231-Bromo-3-chloro-5-fluorobenzene

Product 1

HCID 58337714HCID 58337714, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Bromo-3-chloro-5-fluorobenzene (1.0 g, 4.8 mmol, 1.0 eq), 3-hydroxypyridine (454 mg, 4.77 mmol, 1.00 eq), K2CO3 (792 mg, 5.73 mmol, 1.20 eq) and DMF (15 mL) were added to a microwave vial and microwaved at 200° C. for 30 minutes. The reaction was filtered and concentrated on silica gel (5 g). The silica gel was loaded on top a fresh bed of silica gel and washed with 50% ethyl acetate/hexane. The solvents were removed in vacuo and the crude mixture was purified by flash chromatography on silica gel afforded 950 mg (55%) of the title compound as a golden oil: 1H NMR (400 MHz, CDCl3) δ 8.45-8.44 (m, 2H), 7.58 (dd, J=8.4, 1.5 Hz, 1H), 7.52 (t, J=1.7 Hz, 1H), 7.47 (dd, J=8.5, 4.6 Hz, 1H), 7.25 (t, J=2.1 Hz, 1H), 7.18 (t, J=2.0 Hz, 1H); [M+1]+: 284.0.

Workup

  1. custommicrowaved at 200° C. for 30 minutes
  2. filtrationThe reaction was filtered
  3. concentrationconcentrated on silica gel (5 g)
  4. washwashed with 50% ethyl acetate/hexane
  5. customThe solvents were removed in vacuo
  6. customthe crude mixture was purified by flash chromatography on silica gel

Sources & evidence

ORD record
ord-0074c5cc8fda4a918854f025947a0a1d
Source dataset
uspto-grants-2013_08
Patent number
US08501757B2

Reaction notes

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