1-(Bromomethyl)-4-chlorobenzene → HCID 69345221, compound

HRID 1948227Notes

Reaction equation

HRID 1948227 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5](=[O:8])[NH:6][CH:7]=1.Br[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=1>C1COCC1.CN(C=O)C>[Cl:21][C:18]1[CH:19]=[CH:20][C:15]([CH2:14][N:6]2[CH:7]=[C:2]([Br:1])[CH:3]=[C:4]([C:9]([O:11][CH3:12])=[O:10])[C:5]2=[O:8])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 2763337Methyl 5-bromo-2-hydroxynicotinate

Product 1

HCID 69345221HCID 69345221, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

According to Scheme 1 Step 2: The title compound was prepared from methyl 5-bromo-2-oxo-1,2-dihydropyridine-3-carboxylate (1 eq, 10.0 mmol, 3.00 g) and 1-(bromomethyl)-4-chlorobenzene (1.5 eq, 20.0 mmol, 4.00 g) according to the procedure described for Example 1 Step 2. Reaction conditions: 3 hours at 50° C. in THF/DMF (2:1, 300 mL). The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked 130 g column SiO2) using CH2Cl2/AcOEt 85/15 as the eluent and recrystallized from Et2O to afford the title compound (9.00 mmol, 4.17 g, 90%) as a white solid.

Workup

  1. customReaction conditions
  2. custom3 hours
  3. customat 50° C.
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked 130 g column SiO2)
  5. customrecrystallized from Et2O

Sources & evidence

ORD record
ord-ef6590ac63dc4be1a7bdf34c91e61c84
Source dataset
uspto-grants-2013_03
Patent number
US08399493B2

Reaction notes

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