Acetone → 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone

HRID 1677399ノート

反応式

HRID 1677399 の反応式
[C:1]1([C:7]#[C:8][C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:23]=[C:22]([O:24][CH3:25])[C:21]([O:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=4)[N:16]=3)[NH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.CO.CC(C)=O>C(OCC)(=O)C>[C:1]1([CH2:7][C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([O:28][CH3:29])[C:21]([O:26][CH3:27])=[C:22]([O:24][CH3:25])[CH:23]=4)[N:16]=3)[NH:11][CH:10]=2)=[O:38])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

6

反応物 4

HCID 180AcetoneHCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 595405547-phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine

生成物 1

HCID 442064842-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone収率 206.6%

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

7-Phenylethynyl-2-(3,4,5-trimethoxy-phenyl)-5H-pyrrolo[2,3-b]pyrazine (405 mg, 1.05 mmol) and p-toluenesulfonic acid monohydrate (40 mg, 0.21 mmol) were placed in a 20 ml microwave vial with 14 ml of a 2:1 mixture of methanol and acetone. The reaction was heated in a microwave reactor at 100° C. for 1.5 hours. The reaction was diluted with ethyl acetate, washed two times with saturated sodium bicarbonate and water, dried and concentrated. The residue was triturated with ethyl acetate and hexanes, filtered, and dried to yield 175 mg of 2-phenyl-1-[2-(3,4,5-trimethoxy-phenyl]-5H-pyrrolo[2,3-b]pyrazin-7-yl]-ethanone. MS: (M+H)+=404. MP=226.0-227.0° C.

後処理

  1. washwashed two times with saturated sodium bicarbonate and water
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was triturated with ethyl acetate and hexanes
  5. filtrationfiltered
  6. customdried

出典と根拠

ORDレコード
ord-cc30a89aa5a14234b1695b5f6d3c0b00
出典データセット
uspto-grants-2011_08
特許番号
US08008298B2

反応ノート

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