2-Bromopropane → HCID 66631383, compound

HRID 2093534Notes

Reaction equation

HRID 2093534 reaction equation
[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:22].Br[CH:24]([CH3:26])[CH3:25].C(=O)([O-])[O-].[Cs+].[Cs+]>CN1CCCC1=O>[F:1][C:2]1[C:7]2[C:8]([C:18]([NH:20][CH3:21])=[O:19])=[C:9]([C:11]3[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=3)[O:10][C:6]=2[CH:5]=[CH:4][C:3]=1[O:22][CH:24]([CH3:26])[CH3:25]

Participants

5

Reactant 3

HCID 63582-BromopropaneHCID 10796Cesium carbonateHCID 66631116HCID 66631116, compound

Product 1

HCID 66631383HCID 66631383, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 4-fluoro-2-(4-bromophenyl)-5-hydroxy-N-methylbenzofuran-3-carboxamide (0.17 g, 0.467 mmol, 1 eq), 2-bromopropane (0.18 ml, 1.46 mmol, 3.1 eq), and cesium carbonate (0.46 g, 1.41 mmol, 3 eq) in N-methylpyrrolidinone in a sealed tube was heated at 50° C. for 16 h. The reaction mixture was cooled to r.t., and the inorganic was removed by filtration. The filtrate was diluted with water, and the product extracted into EtOAc. The organic was washed with saturated brine solution, filtered, dried over Na2SO4 and concentrated. The crude product was purified by silica gel (60-120) column chromatography using 0-20% EtOAc in petroleum ether as an eluent Yield: 0.15 g (79.4%). 1H NMR (400 MHz, DMSO-d6) δ 8.66 (d, J=4.4 Hz, 1H), 7.78-7.73 (m, 4H), 7.46 (d, J=9.2 Hz, 1H), 7.26 (t, J=8.4 Hz, 1H), 4.53 (m, 1H), 2.82 (d, J=4.4 Hz, 3H). 1.29 (d, J=6.0 Hz, 6H). Column: purospher@star RP-18 (4×55) mm, 3 μm; Mphase A: 20 mM NH4OAc in 90% H2O, 10% MeCN; Mphase B: 20 mM NH4OAc in 10% H2O, 90% MeCN; Flow: 2.5 ML/min; Time: 0; % A: 100; % B: 0; Time: 1.8; % A: 0; % B: 100; RT min: 2.117, wavelength: 220 nm.

Workup

  1. temperatureThe reaction mixture was cooled to r.t.
  2. customthe inorganic was removed by filtration
  3. additionThe filtrate was diluted with water
  4. extractionthe product extracted into EtOAc
  5. washThe organic was washed with saturated brine solution
  6. filtrationfiltered
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel (60-120) column chromatography
  10. customRT min

Sources & evidence

ORD record
ord-55958f86e4224d6bbc5bfeb42986e08b
Source dataset
uspto-grants-2013_05
Patent number
US08445497B2

Reaction notes

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