Reaction #90446

Reaction equation

product

1-(3,6-dibromo-9H-carbazol-9-yl)-3-phenoxypropan-2-one

2,6-lutidine

O-benzylhydroxylamine hydrochloride

→

white solid

Yield 93.4%

(Z)-1-(3,6-dibromo-9H-carbazol-9-yl)-3-phenoxypropan-2-one O-benzyl oxime

Yield 93.4%

Solvents

THF

Conditions

Workup

1. 1
   Otherconsumption of starting material
2. 2
   OtherThe reaction mixture was quenched with saturated NaHCO3
3. 3
   Extractionextracted 3 times with dichloromethane
4. 4
   DryingThe combined organic extracts were dried with MgSO4
5. 5
   Concentrationconcentrated
6. 6
   Otherto give crude product
7. 7
   OtherIt was further purified by silica gel chromatography (5-10% EtOAc/Hex)

Procedure

To a solution of the product of Step 1 (17.7 mg, 0.0374 mmol, 1.0 equiv) in THF (400 μL) were added 2,6-lutidine (4.4 μL, 0.0374 mmol, 1.0 equiv), O-benzylhydroxylamine hydrochloride (14.3 mg, 0.0898 mmol, 2.4 equiv) and 4A molecular sieves (15.8 mg). The mixture was stirred for 12 h until TLC indicated complete consumption of starting material. The reaction mixture was quenched with saturated NaHCO3 and extracted 3 times with dichloromethane. The combined organic extracts were dried with MgSO4 and concentrated to give crude product. It was further purified by silica gel chromatography (5-10% EtOAc/Hex) to afford 20.2 mg white solid as product, yield 93.4%. 1H NMR (CDCl3, 400 MHz) δ=4.68 (s, 2H) 5.00 (s, 2H) 5.14 (s, 2H) 6.72 (d, J=8.2 Hz, 2H) 6.94 (t, J=7.3 Hz, 1H) 7.47-7.16 (m, 11H) 8.06 (s, 2H)

Source