4-(Bromomethyl)-1-chloro-2-fluorobenzene → 5-(3-methoxyphenethyl)-1-(4-chloro-3-fluorobenzyl)pyridin-2(1H)-one

HRID 1948206Notes

Reaction equation

HRID 1948206 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)=[CH:5][N:4]=1.[Cl:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][C:21]=1[F:28]>>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3](=[O:2])[N:4]([CH2:24][C:23]2[CH:26]=[CH:27][C:20]([Cl:19])=[C:21]([F:28])[CH:22]=2)[CH:5]=1

Participants

3

Reactant 2

HCID 27831364-(Bromomethyl)-1-chloro-2-fluorobenzeneHCID 693454542-Methoxy-5-(2-(3-methoxyphenyl)ethyl)pyridine

Product 1

HCID 589669515-(3-methoxyphenethyl)-1-(4-chloro-3-fluorobenzyl)pyridin-2(1H)-oneYield 60%

Procedure

According to Scheme 8 Step 3: The title compound was prepared from 2-methoxy-5-(2-(3-methoxyphenyl)ethyl)pyridine (1 eq, 0.25 mmol, 0.06 g) and 4-chloro-3-fluorobenzylbromide (2 eq, 0.49 mmol, 0.11 g) according to the procedure described for Example 6 Step 2. Reaction conditions: 12 hours at 100° C. The resulting dark brown oil was purified by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/MeOH 98/2) to afford 5-(3-methoxyphenethyl)-1-(4-chloro-3-fluorobenzyl)pyridin-2(1H)-one (0.14 mmol, 55.0 mg, 60%) as a yellow oil.

Workup

  1. customReaction conditions
  2. custom12 hours
  3. customat 100° C
  4. customThe resulting dark brown oil was purified by flash chromatography (AIT Flashsmart prepacked column 25 g SiO2, CH2Cl2/MeOH 98/2)

Sources & evidence

ORD record
ord-6a865c63ceff463b9d7df7624fd9758d
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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