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

HRID 1621265ノート

反応式

HRID 1621265 の反応式
[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:12][CH2:13][C:14]([O:16]C)=[O:15])=[CH:5][NH:6]2>O1CCCC1.[Li+].[OH-].C(OCC)C>[F:1][C:2]1[CH:10]=[C:9]([F:11])[CH:8]=[C:7]2[C:3]=1[C:4]([S:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:5][NH:6]2

参加物

5

反応物 1

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

生成物 1

HCID 680039162-((4,6-difluoro-1H-indol-3-yl)thio)acetic acid収率 98%

試薬・触媒・溶媒 3

HCID 3283Diethyl Ether溶媒HCID 3939Lithium Hydroxide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

Methyl 2-((4,6-difluoro-1H-indol-3-yl)thio)acetate (253 mg, 0.98 mmol) from Step A was dissolved in a mixture of tetrahydrofuran (8 mL) and 2.0 M aqueous LiOH (2 mL), then stirred vigorously at ambient temperature for 30 minutes. Tetrahydrofuran was removed in vacuo, the aqueous layer neutralized with 1.2 N HCl and extracted with CH2Cl2. The organic layer was dried over magnesium sulfate and removed in vacuo to produce an oily residue. After diluting the residue with diethylether and removing the solvent in vacuo a solid formed which was the desired product (232 mg, 0.95 mmol, 98% yield). LCMS>99% at 254 nm, RT=1.17 min, m/z=244 (M+1).

後処理

  1. customTetrahydrofuran was removed in vacuo
  2. extractionextracted with CH2Cl2
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customremoved in vacuo
  5. customto produce an oily residue
  6. customremoving the solvent in vacuo a solid
  7. customformed which

出典と根拠

ORDレコード
ord-b1b6b9d17c6e45a0a3b8cc8b2af85272
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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