Iodine → 7-Bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2'-oxirane]

HRID 455701ノート

反応式

HRID 455701 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:20](=[CH:21][CH:22]=1)[O:19][C:7]1[C:8]([F:18])=[N:9][C:10]([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[CH:11][C:6]=1[C:5]2=[CH2:23].O.II.C([O-])([O-])=[O:28].[K+].[K+]>C1COCC1.[Ag]=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:5]3([CH2:23][O:28]3)[C:6]3[CH:11]=[C:10]([O:12][CH2:13][C:14]([CH3:17])([CH3:16])[CH3:15])[N:9]=[C:8]([F:18])[C:7]=3[O:19][C:20]2=[CH:21][CH:22]=1

参加物

7

反応物 4

HCID 807IodineHCID 962WaterHCID 11430Potassium CarbonateHCID 673829567-bromo-1-fluoro-5-methylene-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridine

生成物 1

HCID 867619737-Bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2'-oxirane]収率 96.4%

試薬・触媒・溶媒 2

HCID 92152Silver(II) oxide触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-bromo-1-fluoro-5-methylene-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridine (995 mg, 2.63 mmol) in THF (60 mL)/Water (10 mL) was added iodine (1335 mg, 5.26 mmol) and silver oxide (1219 mg, 5.26 mmol). The reaction mixture was allowed to stir at rt for 20 min. K2CO3 (545 mg, 3.95 mmol) was added in one portion and the reaction mixture was allowed to stir for 30 min. The reaction mixture was filtered through a pad of celite. The reaction mixture was partitioned between water and EtOAc. The organic phase was separated, dried over Na2SO4. The solvent was removed under reduced pressure to afford 7-bromo-1-fluoro-3-(neopentyloxy)spiro[chromeno[2,3-c]pyridine-5,2′-oxirane] as a yellow solid (1000 mg) which was taken onto the next step without further purification.

後処理

  1. stirringto stir for 30 min
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. customThe reaction mixture was partitioned between water and EtOAc
  4. customThe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customThe solvent was removed under reduced pressure

出典と根拠

ORDレコード
ord-4a13aafc805946368c57a775fc5318ea
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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