Water → 8-Fluoro-6-(4-fluoro-phenyl)-10-trifluoromethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

HRID 925798ノート

反応式

HRID 925798 の反応式
[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:8]2[N:7]3[CH2:18][CH2:19][NH:20][C:21](=[O:22])[C:6]3=[CH:5][C:4]=2[CH:3]=1.CN(C)CCN(C)C.[F:31][C:32]([F:35])([F:34])I.O>C(#N)C.CN(C=O)C>[F:1][C:2]1[CH:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)[C:8]2[N:7]3[CH2:18][CH2:19][NH:20][C:21](=[O:22])[C:6]3=[C:5]([C:32]([F:35])([F:34])[F:31])[C:4]=2[CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 16843TrifluoroiodomethaneHCID 900360598-Fluoro-6-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one

生成物 1

HCID 733353128-Fluoro-6-(4-fluoro-phenyl)-10-trifluoromethyl-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one収率 34%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6342Acetonitrile溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 8-fluoro-6-(4-fluoro-phenyl)-3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one (example 18) (0.1 g, 0.335 mmol) in acetonitrile (1 ml) and DMF (1 ml), N,N,N′,N′-tetra-methylethylenediamine (77.9 mg, 101 μl, 670 μmol) and tris(2,2′-biryridyl)ruthenium(II)-chloride hexahydrate (5.02 mg, 6.7 μmol) were added at room temperature. The vial was sealed, cooled to −78° C., and with the help of a needle trifluoroiodomethane (˜0.5 ml) was condensed into the reaction tube. A high lumen (6500K) cool daylight lamp was positioned in front of the reaction vial and the reaction was allowed to stir for 40 h at room temperature. The reaction mixture was poured into water (30 ml) and extracted with ethyl acetate (2×40 ml). The combined organic layers were washed with brine (30 ml), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate 20-80%) and trituration (diethyl ether/heptane) to yield the title compound as a white solid (42 mg, 34%), MS (ISP) m/z=367.4 [(M+H)+], mp 193° C.

後処理

  1. customThe vial was sealed
  2. customcondensed into the reaction tube
  3. extractionextracted with ethyl acetate (2×40 ml)
  4. washThe combined organic layers were washed with brine (30 ml)
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customThe crude product was further purified by flash chromatography on silica gel (heptane/ethyl acetate 20-80%) and trituration (diethyl ether/heptane)

出典と根拠

ORDレコード
ord-94dd26d97c044938892eb808e11decac
出典データセット
uspto-grants-2016_03
特許番号
US09284321B2

反応ノート

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