N-Iodosuccinimide → 4-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-one

HRID 1832014Notes

Reaction equation

HRID 1832014 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.IN1C(=O)CC[C:26]1=O>C(#N)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][N:12]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)[C:11](=[O:23])[C:10]=1[CH3:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 220502224-benzyloxy-1-(3-fluorobenzyl)-1H-pyridin-2-one

Product 1

HCID 220499144-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-oneYield 121.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of 4-(benzyloxy)-1-(3-fluorobenzyl)pyridin-2(1H)-one (4.83 g, 15.6 mmol) and N-iodosuccinimide (NIS, 3.86 g, 17.1 mmol) in anhydrous acetonitrile (55 mL) was heated at 65° C. for 4 hours under nitrogen atmosphere. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (ethyl acetate/hexane 1:1 v/v). The appropriate fractions were collected according to ES MS (M+H 436) and washed with Na2SO3 to remove the color impurities. The fractions were concentrated under reduced pressure and dried in vacuo to afford the desired product (6.15 g, 90%) as a light yellow solid. 1H-NMR (CD3OD, 400 MHz) δ 7.73 (d, 1H, J=7.6 Hz), 7.36 (m, 6H), 7.08 (m, 3H), 6.39 (d, 1H, J=8.0 Hz), 5.28 (s, 2H), 5.19 (s, 2H); ES-HRMS m/z 436.0196 (M+H calculated for C19H16NO2FI requires 436.0210). Step 2. Preparation of 4-(benzyloxy)-1-(3-fluorobenzyl)-3-methylpyridin-2(1H)-one

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (ethyl acetate/hexane 1:1 v/v)
  3. customThe appropriate fractions were collected
  4. washwashed with Na2SO3
  5. customto remove the color impurities
  6. concentrationThe fractions were concentrated under reduced pressure
  7. customdried in vacuo

Sources & evidence

ORD record
ord-402e45a7e62f4457ac639de075b9c99b
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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