Dimethylformamide → HCID 68701183, 화합물

HRID 14504노트

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HRID 14504 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

HCID 68701183HCID 68701183, 화합물

시약·촉매·용매 3

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

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온도
180 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-3ba665b8e1054935a1a2c1ba98a264df
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732435B2

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