(2-amino-5-bromophenyl)-(2-fluorophenyl)methanone

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (2-amino-5-bromophenyl)(2-fluorophenyl)methanone (15 g, 51.0 mmol) and sodium bicarbonate (12.85 g, 153 mmol) in CHCl3 (150 mL) was cooled in an ice bath to 0° C. A solution of 2-bromoacetyl bromide (4.89 mL, 56.1 mmol) was added drop-wise slowly and washed in with CHCl3 (30 ml). The cooling was removed and the mixture was stirred for 2 hr. washed in with CHCl3 (30 ml) The cooling was removed

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 20 g of 2-amino-5-bromo-2'-fluorobenzophenone are heated at 85° C. for 48 hours in 120 ml of dry pyridine in the presence of 20 g of 3,4-dimethoxyphenylsulfonyl chloride. The mixture is cooled, poured into ice-cold water, the solid is filtered off, the solid is extracted with AcOEt, the organic phase is washed with water, a solution of hydrochloric acid (1N), water and then saline water. After drying over magnesium sulfate and evaporating the solvent under vacuum, a solid is obtained which is recrystallized from DCM/isopropyl ether. The mixture is cooled poured into ice-cold water the solid is filtered off the solid is extracted with AcOEt the organic phase is washed with water After drying over magnesium sulfate evaporating the solvent under vacuum a solid is obtained which is recrystallized from DCM/isopropyl ether

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A round-bottomed flask was charged with (2-amino-5-bromophenyl)(2-fluorophenyl)methanone (1.45 g), 9H-fluoren-9-ylmethyl (2-chloro-2-oxoethyl)carbamate (1.6 g) and chloroform (150 mL). The mixture was heated to reflux for 2 h then concentrated to dryness. The residue was taken up in a mixture of a saturated solution of sodium bicarbonate and ethyl acetate. The resulting solids were collected on a filter and washed first with water then with diethyl ether. Thorough air-drying provided 9H-fluoren-9-ylmethyl [2-({4-bromo-2-[(2-fluorophenyl)carbonyl]phenyl}amino)-2-oxoethyl]carbamate (2 g) as a light yellow powder. H1 NMR (d6-dmso): 10.8 (br s, 1H), 7.95 (d, 1H), 7.75-7.90 (m, 4H), 7.45-7.70 (m, 5H), 7.20-7.42 (m, 6H), 4.30 (d, 2H), 4.20 (t, 1H), 3.65 (d, 2H). The mixture was heated to reflux for 2 h then concentrated to dryness The residue was taken up in a mixture of a saturated solution of sodium bicarbonate and ethyl acetate The resulting solids were collected on a filter washed first with water