Sodium Carbonate → 5-(6-Bromo-pyridin-2-yl)-5-fluoromethyl-morpholin-3-one

HRID 474049ノート

反応式

HRID 474049 の反応式
[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH2:15]O)[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.C(N(S(F)(F)[F:23])CC)C.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]2([CH2:15][F:23])[NH:13][C:12](=[O:14])[CH2:11][O:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 3

HCID 10340Sodium CarbonateHCID 123472(Diethylamino)sulfur trifluorideHCID 866680225-(6-Bromo-pyridin-2-yl)-5-hydroxymethyl-morpholin-3-one

生成物 1

HCID 866680235-(6-Bromo-pyridin-2-yl)-5-fluoromethyl-morpholin-3-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 5-(6-bromo-pyridin-2-yl)-5-hydroxymethyl-morpholin-3-one (2.8 g, 9.756 mmol) in dry THF (30 ml), diethylamino sulfur trifluoride (4.72 g, 29.268 mmol) was added at rt and stirring continued for 4 h. Na2CO3 was then added to the resultant reaction mixture and stirred for further 30 min. The reaction mixture was concentrated under reduced pressure and the product was extracted with ethyl acetate. Organic layer was washed with brine, dried over anhy. Na2SO4 and concentrated under reduced pressure to obtain crude compound as gummy residue. Purification of the crude product with 45% ethyl acetate in hexane solvent system furnished the title compound as off-white solid. Yield=1.15 g (40%). TLC (70% ethyl acetate in hexane) Rf=0.49; LCMS: RtH7=0.383, [M+1]+=289 and 289; HPLC RtH9=3.27 min (84%); 1H NMR (400 MHz, CDCl3): δ 7.62 (t, 1H), 7.49 (dd, 1H), 7.32 (d, 1H), 7.09 (br. s, 1H), 4.92 (dd, 1H), 4.52 (dd, 1H), 4.32-4.17 (m, 3H), 3.98-3.93 (dd, 1H); 19F NMR (376.2 MHz): δ−255.65 (t, 1F).

後処理

  1. customreaction mixture
  2. stirringstirred for further 30 min
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. extractionthe product was extracted with ethyl acetate
  5. washOrganic layer was washed with brine
  6. customdried over anhy
  7. concentrationNa2SO4 and concentrated under reduced pressure
  8. customto obtain crude compound as gummy residue
  9. customPurification of the crude product with 45% ethyl acetate in hexane solvent system

出典と根拠

ORDレコード
ord-67561828413147f7913a8fa28cce7a30
出典データセット
uspto-grants-2014_01
特許番号
US08637508B2

反応ノート

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