Ammonium formate → 6-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine

HRID 1847597ノート

反応式

HRID 1847597 の反応式
[F:1][C:2]1[C:3]([N+:16]([O-])=O)=[CH:4][C:5]2[CH:6]=[C:7]3[C:13]([CH3:15])([CH3:14])[CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[F:1][C:2]1[C:3]([NH2:16])=[CH:4][C:5]2[CH:6]=[C:7]3[C:13]([CH3:14])([CH3:15])[CH2:12][CH2:11][N:8]3[C:9]=2[CH:10]=1

参加物

5

反応物 2

HCID 2723923Ammonium formateHCID 591295786-fluoro-1,1-dimethyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole

生成物 1

HCID 581832876-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine収率 49.6%

試薬・触媒・溶媒 2

HCID 23938Palladium触媒HCID 702Ethanol溶媒

実験手順

To a solution of 6-fluoro-1,1-dimethyl-7-nitro-2,3-dihydro-1H-pyrrolo[1,2-a]indole (600 mg, 2.4 mmol) in ethanol (15 mL) was added ammonium formate (600 mg, 9.5 mmol) and Pd/C (10%, 129 mg, 0.12 mmol). The mixture was refluxed for 10 min. The Pd catalyst was removed via filtration through Celite and washed with ethanol. The filtrate was concentrated and purified by column chromatography (20-40% ethyl acetate-hexanes) to provide 6-fluoro-1,1-dimethyl-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-amine (260 mg, 49%). ESI-MS m/z calc. 218.1, found 219.2 (M+1)+. Retention time 1.01 minutes.

後処理

  1. temperatureThe mixture was refluxed for 10 min
  2. customThe Pd catalyst was removed via filtration through Celite
  3. washwashed with ethanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (20-40% ethyl acetate-hexanes)

出典と根拠

ORDレコード
ord-8173d011b602403f84e77e5aae9a3d5d
出典データセット
uspto-grants-2015_02
特許番号
US08952050B2

反応ノート

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