Water → 2-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid methyl ester

HRID 1963092ノート

反応式

HRID 1963092 の反応式
[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[CH3:22])=[CH:7][N:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]2)=[O:4].I[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C([O-])(=O)C.[K+].O>CN1C(=O)CCC1.C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][O:2][C:3]([C:5]1[C:6]([CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[CH3:22])=[C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[N:8]2[C:13]=1[CH:12]=[CH:11][CH:10]=[CH:9]2)=[O:4]

参加物

8

反応物 4

HCID 962WaterHCID 11575IodobenzeneHCID 517044Potassium AcetateHCID 677725592-(3-Fluoro-2-methyl-benzyl)indolizine-1-carboxylic acid methyl ester

生成物 1

HCID 677721232-(3-Fluoro-2-methyl-benzyl)-3-phenyl-indolizine-1-carboxylic acid methyl ester収率 32.4%

試薬・触媒・溶媒 3

HCID 178418476HCID 178418476、化合物触媒HCID 6344Dichloromethane溶媒HCID 13387N-methyl-2-pyrrolidone溶媒

実験手順

The compound of step 2 (1.79 g, 6.02 mmol), iodo-benzene (1.47 g, 7.22 mmol), potassium acetate (1.18 g, 12.03 mmol) and bis(triphenylphosphine)palladium(II) chloride (844 mg, 1.20 mmol) in NMP were heated at 100° C. for 10 min under argon. Then water (844 mg, 36.10 mmol) was added and heating continued for 12 h. The mixture was cooled to room temperature, diluted with DCM and washed with water. The organic phase was dried over sodium sulfate, and evaporated. The residue was purified by silica gel chromatography (HEP/EA) to give 729 mg of the title compound.

後処理

  1. temperatureheating
  2. washwashed with water
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography (HEP/EA)

出典と根拠

ORDレコード
ord-e1a768efc37e48a799de33a4a4a29ab8
出典データセット
uspto-grants-2013_04
特許番号
US08415336B2

反応ノート

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