Sodium Carbonate → Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate

HRID 1479595노트

반응식

HRID 1479595 반응식
C(O[C:6]([NH:8][C:9]1[CH:14]=[C:13]([C:15]([O:17][CH3:18])=[O:16])[CH:12]=[CH:11][C:10]=1B(O)O)=O)(C)(C)C.ClC1N=C(CCC2C=CC=CC=2)C=CC=1C#[N:26].Cl[C:40]1[C:41](C#N)=[N:42][CH:43]=[C:44](/[CH:46]=[CH:47]/[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH:45]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.CCOC(C)=O.O>[NH2:26][C:6]1[C:41]2[N:42]=[CH:43][C:44]([CH2:46][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[CH:45][C:40]=2[C:10]2[CH:11]=[CH:12][C:13]([C:15]([O:17][CH3:18])=[O:16])=[CH:14][C:9]=2[N:8]=1

참가 물질

8

반응물 4

HCID 10340Sodium CarbonateHCID 668752372-(Tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenylboronic acidHCID 66875239(E)-3-chloro-5-styrylpicolinonitrileHCID 856827592-Chloro-6-phenethylnicotinonitrile

생성물 1

HCID 66874950Methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate

시약·촉매·용매 3

HCID 962Water용매HCID 8857Ethyl Acetate용매HCID 21863594Toluene ethanol용매

반응 조건

온도
100 °C

실험 절차

A solution of 2-(tert-butoxycarbonylamino)-4-(methoxycarbonyl)phenylboronic acid (from Example 85/Step 1) (1.0 eq.) and 2-chloro-6-phenethylnicotinonitrile (prepared from (E)-3-chloro-5-styrylpicolinonitrile (from Example 32/Step 1) following the procedure described in Example 114/Step 3) (1.0 eq.), tetrakis(triphenyl-phosphine)palladium (5 mol %), and 2N aqueous sodium carbonate solution (2.0 eq.) in toluene/ethanol (2:1, 0.03 M) was stirred at 100° C. overnight. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and water. The two phases were separated, and the aqueous layer was extracted twice with EtOAc. The combined organic layers were washed with brine, dried over anhydrous MgSO4, and concentrated en vaccuo. The crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO) using 0-60% EtOAc/Hexanes to give methyl 5-amino-2-phenethylbenzo[f][1,7]naphthyridine-8-carboxylate as a white solid.

후처리

  1. temperatureAfter cooling to ambient temperature
  2. customThe two phases were separated
  3. extractionthe aqueous layer was extracted twice with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated en vaccuo
  7. customThe crude material was purified by flash chromatography on a COMBIFLASH® system (ISCO)

출처 및 근거

ORD 기록
ord-f9576cd1471345dbaad723de5125df0a
출처 데이터셋
uspto-grants-2016_08
특허 번호
US09408907B2

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