Dichloromethane → 2-(3-fluoro-4-hydroxyphenylamino)-N-(4-fluorophenyl)nicotinamide

HRID 2241394Notes

Reaction equation

HRID 2241394 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[O:8]C.C(Cl)Cl.B(Br)(Br)Br.C([O-])(O)=O.[Na+]>O>[F:1][C:2]1[CH:3]=[C:4]([NH:10][C:11]2[N:26]=[CH:25][CH:24]=[CH:23][C:12]=2[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[O:14])[CH:5]=[CH:6][C:7]=1[OH:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 672215822-(3-fluoro-4-methoxyphenylamino)-N-(4-fluorophenyl)nicotinamide

Product 1

HCID 672218842-(3-fluoro-4-hydroxyphenylamino)-N-(4-fluorophenyl)nicotinamideYield 81.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A 250 mL round-bottomed flask was charged with 2-(3-fluoro-4-methoxyphenylamino)-N-(4-fluorophenyl)nicotinamide (8.00 g, 22.5 mmol) and DCM (75 mL). The reaction mixture was cooled to 0° C. and BBr3 (10.9 ml, 115 mmol) was added dropwise over 5 minutes. The reaction mixture was stirred for 2 hours, then slowly quenched by pipetting the reaction into a flask (500 mL) containing saturated NaHCO3 (20 mL), water (150 mL). This solution was extracted with EtOAc. The organic layer was dried and concentrated to provide the product 6.25 g (73%). LRMS M−1 (339.9) observed.

Workup

  1. customslowly quenched
  2. customthe reaction into a flask (500 mL)
  3. extractionThis solution was extracted with EtOAc
  4. customThe organic layer was dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fc5a65088d6e41358766918ae03e4e1e
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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