Iodine → Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate

HRID 1621264ノート

反応式

HRID 1621264 の反応式
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[C:12]([O:16][CH3:17])(=[O:15])[CH2:13][SH:14].II.[I-].[K+]>CO.O>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:14][CH2:13][C:12]([O:16][CH3:17])=[O:15])=[CH:5][NH:6]2

参加物

7

反応物 4

HCID 807IodineHCID 4875Potassium IodideHCID 16907Methyl ThioglycolateHCID 27787364,6-difluoro-1H-indole

生成物 1

HCID 68004081Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate収率 19%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a solution of 4,6-difluoro-indole (1.00 g, 6.53 mmol) and methyl thioglycolate (584 μL, 6.53 mmol) in methanol:water (25 mL:7.0 mL) was added iodine (1.65 g, 6.53 mmol) and potassium iodide (1.09 g, 6.53 mmol). The reaction mixture was stirred at ambient temperature for 60 hours. Methanol was removed in vacuo and the aqueous layer diluted with a saturated solution of sodium bicarbonate and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate, evaporated in vacuo and the resulting residue was purified on a silica gel column (0-100% ethyl acetate:hexanes over 19 min) to afford the desired product (253 mg, 19% yield). LCMS>98% at 254 nm, RT=1.33 min, m/z=258 (M+1).

後処理

  1. customMethanol was removed in vacuo
  2. additionthe aqueous layer diluted with a saturated solution of sodium bicarbonate
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. customevaporated in vacuo
  6. customthe resulting residue was purified on a silica gel column (0-100% ethyl acetate:hexanes over 19 min)

出典と根拠

ORDレコード
ord-e76914fa45a24e6eab541118a9d12d9d
出典データセット
uspto-grants-2014_07
特許番号
US08772509B2

反応ノート

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