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Dimethylformamide → HCID 69200517, 화합물

HRID 1745813
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HRID 1745813 반응식
[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12](Br)[CH:13]=2)[CH:8]=[N:7][CH:6]=1.[CH3:17][N:18](C=O)C>C(Cl)(Cl)Cl.[C-]#N.[C-]#N.[Zn+2].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].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]>[CH3:1][O:2][C:3](=[O:16])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:17]#[N:18])[CH:13]=2)[CH:8]=[N:7][CH:6]=1
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참가 물질

7

반응물 2

HCID 6228DimethylformamideHCID 69199203HCID 69199203, 화합물

생성물 1

HCID 69200517HCID 69200517, 화합물

시약·촉매·용매 4

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)촉매
HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 6212Chloroform용매

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온도
120 °C

실험 절차

A solution of (6-bromo-isoquinolin-4-yl)-acetic acid methyl ester (52 mg, 0.19 mmol), prepared as described as an intermediate for Intermediate 31, in DMF (3 ml) is added to zinc dicyanide (26 mg, 0.22 mmol) under a nitrogen atmosphere. To the resulting mixture is added 1,1′-bis(diphenylphosphino)ferrocene (15 mg) and tris(dibenzylideneacetone)dipalladium(0) (8 mg) and the resulting mixture stirred at 120° C. for 22 h. The solution is cooled and diluted with chloroform (30 ml) and washed with water (2×20 ml) followed by brine (20 ml). Further chloroform is added (40 ml) and the solution dried over MgSO4, filtered and concentrated. Repetitive flash silica column chromatography (eluants 40:1 CH2Cl2:methanol, then 50:1 CH2Cl2:methanol) gives (6-cyano-isoquinolin-4-yl)-acetic acid methyl ester [MH]+ 227. This intermediate is saponified by treatment with LiOH in 3:1 THF/water. The resulting mixture is partially evaporated to remove the THF, diluted to 10 ml with water then washed with ethyl acetate. The aqeous phase is then neutralised with 1M hydrochloric acid (to pH 4-5) and exhaustively extracted with ethylacetate. The organic phase is dried over MgSO4, filtered and concentrated to give (6-cyano-isoquinolin-4-yl)-acetic acid M+ 212.

후처리

  1. temperatureThe solution is cooled
  2. washwashed with water (2×20 ml)
  3. additionFurther chloroform is added (40 ml)
  4. dry with materialthe solution dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-11e8dfcf1dc24573b4abe43cf9988c98
출처 데이터셋
uspto-grants-2006_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07019136B2

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