3-Bromo-o-toluidine → HCID 59375104, compound

HRID 661871Notes

Reaction equation

HRID 661871 reaction equation
[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].F[C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=1.CC(C)([O-])C.[K+]>CS(C)=O>[Br:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:11]2[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=2)[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 1235383-Bromo-o-toluidineHCID 27374032-Fluoro-4-methylpyridineHCID 23665647Potassium tert-butoxide

Product 1

HCID 59375104HCID 59375104, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
190 °C

Procedure

A mixture of 3-bromo-2-methylaniline (200 mg, 1.075 mmol), 2-fluoro-4-methylpyridine (155 mg, 1.397 mmol) and potassium tert-butoxide (193 mg, 1.72 mmol) in DMSO (4 mL) was heated in a sealed tube via microwave irradiation at 190° C. for 40 min. The mixture was partitioned between EtOAc and water, and the organic phase was washed with brine, dried and concentrated. The residue was purified by column chromatography (eluting with a gradient from hexane to 85:15 hexane-EtOAc) to provide N-(3-bromo-2-methylphenyl)-4-methylpyridin-2-amine as a yellow solid (100 mg, 34%). 1H NMR (400 MHz, chloroform-d) δ 8.05 (1H, d, J=5.3 Hz), 7.38 (2H, d, J=8.1 Hz), 7.06 (1H, t, J=8.0 Hz), 6.58 (1H, d, J=5.3 Hz), 6.40 (1H, s), 6.23 (1H, br. s.), 2.37 (3H, s), 2.23 (3H, s). Mass spectrum m/z 277, 279 (M+H)+.

Workup

  1. customThe mixture was partitioned between EtOAc and water
  2. washthe organic phase was washed with brine
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (
  6. washeluting with a gradient from hexane to 85:15 hexane-EtOAc)

Sources & evidence

ORD record
ord-20f00165ab464952833446116ced8ec6
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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