Methanol → HCID 69345556, compound

HRID 1948217Notes

Reaction equation

HRID 1948217 reaction equation
B(Br)(Br)Br.[F:5][C:6]1[CH:27]=[C:26]([Cl:28])[CH:25]=[CH:24][C:7]=1[CH2:8][N:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[CH:19][C:18]([O:21]C)=[CH:17][CH:16]=2)[CH:12]=[CH:11][C:10]1=[O:23].CO>C(Cl)Cl>[Cl:28][C:26]1[CH:25]=[CH:24][C:7]([CH2:8][N:9]2[CH:14]=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH:12]=[CH:11][C:10]2=[O:23])=[C:6]([F:5])[CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromide2×HCID 115230231-[(4-Chloro-2-fluorophenyl)methyl]-5-(4-methoxyphenyl)-2(1H)-pyridinone

Product 1

HCID 69345556HCID 69345556, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-40 °C

Procedure

According to Scheme 14 Step 1: BBr3 (4 eq, 65.6 mmol, 6.56 mL) was added to a solution of 1-(2-fluoro-4-chlorobenzyl)-5-(4-methoxyphenyl)pyridin-2(1H)-one (16.4 mmol, 5.64 g) in CH2Cl2 at −50° C. The reaction mixture was stirred 1.5 hour at −40° C., overnight at room temperature then BBr3 (20 mL) was added at −30° C. and the reaction mixture was stirred 4 hours at room temperature. The reaction mixture was cooled down to −40° C. then MeOH (50 mL) was added dropwise and the crude mixture was stirred at room temperature. After evaporation, the crude mixture was purified by silica gel chromatography (300 g SiO2) using CH2Cl2/MeOH 95/5 to afford 1-(4-chloro-2-fluorobenzyl)-5-(4-hydroxyphenyl)pyridin-2(1H)-one (14.9 mmol, 4.80 g, 83%) as an orange solid.

Workup

  1. stirringthe reaction mixture was stirred 4 hours at room temperature
  2. temperatureThe reaction mixture was cooled down to −40° C.
  3. customAfter evaporation
  4. customthe crude mixture was purified by silica gel chromatography (300 g SiO2)

Sources & evidence

ORD record
ord-e0d166a2869844f4a8d4a8317002b7bb
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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