Triethylamine → HCID 54724205, compound

HRID 1831979Notes

Reaction equation

HRID 1831979 reaction equation
Br[C:2]1[C:3](=[O:18])[N:4]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([F:17])[CH:12]=2)[C:5]([CH3:9])=[CH:6][C:7]=1[OH:8].C(N(CC)CC)C>ClCCl>[F:17][C:13]1[CH:12]=[C:11]([CH:16]=[CH:15][CH:14]=1)[CH2:10][N:4]1[C:5]([CH3:9])=[CH:6][C:7]([OH:8])=[CH:2][C:3]1=[O:18]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 54724200HCID 54724200, compound

Product 1

HCID 54724205HCID 54724205, compoundYield 153.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-30 °C

Procedure

To a suspension of 3-bromo-1-(3-fluorobenzyl)-4-hydroxy-6-methylpyridin-2(1H)-one (0.86 g, 0.0028 mol) in dichloromethane (15.0 mL) cooled to −30° C., triethyl amine (0.5 mL, 0.004 mol) and trflic anhydride (0.7 mL, 0.0042 mol) were added and stirred for 1 h. The resulting orange solution was poured into ice cold water (25 mL) and extracted with dichloromethane (2×25 mL) The combined organic extracts were washed with water, dried (Na2SO4) and concentrated under reduced pressure. The resulting residue was purified by silica gel flash chromatography using 1:1 EtOAc/hexane v/v to afford 1.0 g (85%) the title compound as a light brown solid: 1H-NMR (CDCl3/400 MHz) δ 7.32 (m, 1H), 7.0-6.85 (m, 3H), 6.18 (s, 1H), 5.32 (s, 2H), and 2.34 (s, 3H); ES HRMS m/z 443.9492 (M+H C14H11NO4BrF4S requires 443.9528). Step 4: Preparation of 3-bromo-1-(3-fluorobenzyl)-6-methyl-4-(phenylethynyl)pyridin-2(1H)-one

Workup

  1. extractionextracted with dichloromethane (2×25 mL) The combined organic extracts
  2. washwere washed with water
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-3b3ec51c031b499a8294de9c4fbebb36
Source dataset
uspto-grants-2006_06
Patent number
US07067540B2

Reaction notes

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