Potassium Carbonate → HCID 69349998, compound

HRID 1948187Notes

Reaction equation

HRID 1948187 reaction equation
C([O-])([O-])=O.[K+].[K+].Br[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[F:16].[Br:17][C:18]1[CH:19]=[CH:20][C:21](=[O:24])[NH:22][CH:23]=1>C1COCC1>[Cl:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:22]2[CH:23]=[C:18]([Br:17])[CH:19]=[CH:20][C:21]2=[O:24])=[C:10]([F:16])[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5995285-Bromo-2-hydroxypyridineHCID 27365514-Chloro-2-fluorobenzyl bromide

Product 1

HCID 69349998HCID 69349998, compoundYield 82.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

According to Scheme 1 Step 2: K2CO3 (10 eq, 0.11 mmol, 16.0 g) and 1-(bromomethyl)-4-chloro-2-fluorobenzene (1.5 eq, 17.0 mmol, 3.90 g) was added to a solution of 5-bromopyridin-2(1H)-one (1 eq, 11.0 mmol, 2.00 g), in THF (100 mL). The suspension was stirred for 2 hours at room temperature and 17 hours at 60° C. The reaction mixture was filtered and the mother liquor was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2) using CH2Cl2/AcOEt 80/20 as eluent to afford the title compound 1-(4-chloro-2-fluorobenzyl)-5-bromopyridin-2(1H)-one (9.10 mmol, 2.87 g, 79%) as a white solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe mother liquor was concentrated under reduced pressure
  3. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2)

Sources & evidence

ORD record
ord-1d6f4923e00341fd91394cf82cf347d2
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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