Dimethylformamide → HCID 68701183、化合物

HRID 14504ノート

反応式

HRID 14504 の反応式
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:21](=[O:22])[C:20]3[C:11](=[C:12]4[C:17](=[CH:18][CH:19]=3)[NH:16][CH2:15][CH2:14][O:13]4)[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.[CH3:26][N:27](C)C=O>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].[C-]#N.[Zn+2].[C-]#N>[CH:23]([C:9]1[O:10][C:11]2[C:20]([C:21](=[O:22])[C:8]=1[C:5]1[CH:6]=[CH:7][C:2]([C:26]#[N:27])=[CH:3][CH:4]=1)=[CH:19][CH:18]=[C:17]1[C:12]=2[O:13][CH2:14][CH2:15][NH:16]1)([CH3:25])[CH3:24]

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 167498117-(4-Chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one

生成物 1

HCID 68701183HCID 68701183、化合物

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
180 °C

実験手順

A mixture of 7-(4-chlorophenyl)-6-isopropyl-2,3-dihydro-1H-1-aza-4,5-dioxa-phenanthren-8-one (71.7 mg, 0.202 mmol), tris(dibenzylideneacetone)dipalladium (0) (92.2 mg, 0.101 mmol), 1,1′-bis(diphenylphosphino)ferrocene (112 mg, 0.202 mmol) and zinc cyanide (24 mg, 0.204 mmol) in N,N-dimethylformamide (2.5 ml) is heated at 180° C. for 40 min under microwave irradiation in an Emrys Optimizer instrument (Biotage AB, Uppsala, Sweden). The mixture is filtered through a short pad of Celite, which is then thoroughly washed through with ethyl acetate. The filtrate is washed successively with water and brine. The organic layer is dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient) to afford the title compound.

後処理

  1. filtrationThe mixture is filtered through a short pad of Celite, which
  2. washis then thoroughly washed through with ethyl acetate
  3. washThe filtrate is washed successively with water and brine
  4. dry with materialThe organic layer is dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by flash chromatography (cyclohexane/ethyl acetate gradient)

出典と根拠

ORDレコード
ord-3ba665b8e1054935a1a2c1ba98a264df
出典データセット
uspto-grants-2010_06
特許番号
US07732435B2

反応ノート

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