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Cesium carbonate → 6-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide

HRID 1961477
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HRID 1961477 반응식
[C:1]([C:5]1[CH:26]=[CH:25][C:8]([CH2:9][NH:10][C:11]([C:13]2[C:14]([CH3:24])=[N:15][C:16]3[C:21]([CH:22]=2)=[CH:20][C:19](I)=[CH:18][N:17]=3)=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:27]([O-:30])([O-])=O.[Cs+].[Cs+].CC1C=N[C:37]2[C:46](C=1C)=[CH:45][CH:44]=[C:43]1[C:38]=2N=CC(C)=C1C>C(O)C1C=CC=CC=1.[Cu]I>[CH2:27]([O:30][C:19]1[CH:20]=[C:21]2[C:16](=[N:17][CH:18]=1)[N:15]=[C:14]([CH3:24])[C:13]([C:11]([NH:10][CH2:9][C:8]1[CH:25]=[CH:26][C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])=[CH:6][CH:7]=1)=[O:12])=[CH:22]2)[C:37]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:38]=1
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참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 742653,4,7,8-Tetramethyl-1,10-phenanthrolineHCID 66746137N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide

생성물 1

HCID 667454906-(benzyloxy)-N-(4-tert-butylbenzyl)-2-methyl-1,8-naphthyridine-3-carboxamide수율 235.1%

시약·촉매·용매 2

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 244Benzyl Alcohol용매

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온도
120 °C

실험 절차

In a screw cap pressure tube were N-(4-tert-butylbenzyl)-6-iodo-2-methyl-1,8-naphthyridine-3-carboxamide (135 mg, 0.30 mmol), Cs2CO3 (191.5 mg, 0.6 mmol), CuI (5.6 mg, 0.03 mmol) and 3,4,7,8-tetramethyl-1,10-phenantroline (14.0 mg, 0.06 mmol)) suspended in benzyl alcohol (4.5 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 120° C. overnight. The mixture was allowed to cool. CH2Cl2 was added and the mixture washed with H2O, dried (MgSO4), filtered and concentrated. The crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3) yielding 62 mg of the title compound (47%).

후처리

  1. customIn a screw cap pressure tube
  2. customN2 was bubbled through the suspension for 5 min
  3. customThe tube was sealed
  4. temperatureto cool
  5. additionCH2Cl2 was added
  6. washthe mixture washed with H2O
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude mixture was purified by flash chromatography (CH2Cl2/MeOH 98:2→97:3)

출처 및 근거

ORD 기록
ord-6d277d7471d1496ab58ea35c98806e13
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415333B2

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