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Sodium Carbonate → Dactolisib

HRID 2199274
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HRID 2199274 반응식
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3](B(O)O)[CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].Br[C:21]1[CH:30]=[CH:29][C:28]2[N:27]=[CH:26][C:25]3[N:31]([CH3:46])[C:32](=[O:45])[N:33]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([CH3:44])([CH3:43])[C:41]#[N:42])=[CH:36][CH:35]=4)[C:24]=3[C:23]=2[CH:22]=1>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:44][C:40]([C:37]1[CH:36]=[CH:35][C:34]([N:33]2[C:24]3[C:23]4[CH:22]=[C:21]([C:3]5[CH:2]=[N:1][C:10]6[C:5]([CH:4]=5)=[CH:6][CH:7]=[CH:8][CH:9]=6)[CH:30]=[CH:29][C:28]=4[N:27]=[CH:26][C:25]=3[N:31]([CH3:46])[C:32]2=[O:45])=[CH:39][CH:38]=1)([CH3:43])[C:41]#[N:42]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 426095702-(4-(8-Bromo-3-methyl-2-oxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-1-yl)phenyl)-2-methylpropanenitrile

생성물 1

HCID 11977753Dactolisib

시약·촉매·용매 2

HCID 178419050HCID 178419050, 화합물촉매
HCID 6228
Dimethylformamide
용매

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온도
100 °C

실험 절차

0.3 mmol of 3-quinoline boronic acid (Aldrich, Buchs, Switzerland), 8 mg of bis(triphenylphosphine)palladium (II) dichloride (Fluka, Buchs, Switzerland) and 0.5 ml of a 1 M solution of Na2CO3 are added to a solution of 84 mg (0.2 mmol) of 2-[4-(8-bromo-3-methyl-2-oxo-2,3-dihydro-imidazo[4,5-c]quinolin-1-yl)-phenyl]-2-methyl-propionitrile (Example 1i) in 2 ml of DMF. The mixture is stirred for 1 h. at 100° C. After this time, the mixture is quenched with sat. aqueous NaHCO3 and extracted with EtOAc (2×). The organic layer is washed with brine, dried over Na2SO4, filtered and evaporated in vacuo. The residue is loaded on silica gel and purified by flash chromatography to give the title compound. ES-MS: 470 (M+H)+; analytical HPLC: tret=2.90 min (Grad 1).

후처리

  1. customAfter this time, the mixture is quenched with sat. aqueous NaHCO3
  2. extractionextracted with EtOAc (2×)
  3. washThe organic layer is washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-6a30c85225024725b6c115bd2d69dc8c
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09358229B2

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