Potassium Carbonate → 2,6a,8,11-Tetraazabenzo[a]fluorene

HRID 921045노트

반응식

HRID 921045 반응식
[NH2:1][C:2]1[C:11]2[C:6](=[CH:7][C:8](C(C)(C)C)=[N:9][CH:10]=2)[CH:5]=[CH:4][N:3]=1.C([C:20]1[C:25](Br)=[C:24](I)[CH:23]=[CH:22][N:21]=1)(C)(C)C.FC(F)(F)C1C=C(I)C(Cl)=CN=1.C(=O)([O-])[O-].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC1C=CC=CC=1C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:10]1[C:11]2[C:2]3[N:3]([CH:4]=[CH:5][C:6]=2[CH:7]=[CH:8][N:9]=1)[C:23]1[C:24](=[CH:25][CH:20]=[N:21][CH:22]=1)[N:1]=3

참가 물질

8

반응물 5

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 587173846-Tert-butyl-2,7-naphthyridin-1-amine2회HCID 674788695-Chloro-4-iodo-2-(trifluoromethyl)pyridineHCID 679953862-tert-Butyl-3-bromo-4-iodopyridine

생성물 1

HCID 866802552,6a,8,11-Tetraazabenzo[a]fluorene

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 7237O-Xylene용매

실험 절차

A vigorously stirred mixture of 20.1 g (100 mmol) of 1-amino-6-tert-butyl-2,7-naphthyridine S41, 37.4 g (110 mmol) of 2-tert-butyl-3-bromo-4-iodopyridine (S27) or 27.9 g (110 mmol) of 2-trifluoromethyl-4-iodo-5-chloropyridine, 35.0 g (250 mmol) of potassium carbonate, 200 g of glass beads (diameter 3 mm), 2.6 g (10 mmol) of triphenylphosphine and 450 mg (2 mmol) of palladium(II) acetate in 500 ml of o-xylene is heated under reflux until the 1-amino-6-tert-butyl-2,7-naphthyridine has been consumed (typically 3-30 h). After cooling, the solid is filtered off via a silica-gel bed, rinsed with 1000 ml of THF, and the filtrate is evaporated to dryness. The residue is dissolved in 75 ml of ethyl acetate at the boiling temperature, and 250 ml of n-heptane are slowly added. After cooling, the solid which has crystallised out is filtered off with suction, washed twice with 50 ml of n-heptane each time and dried in vacuo. The solids obtained in this way are freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 170-200° C.). Purity according to 1H-NMR typically >99.5%.

후처리

  1. temperatureis heated
  2. customhas been consumed (typically 3-30 h)
  3. temperatureAfter cooling
  4. filtrationthe solid is filtered off via a silica-gel bed
  5. washrinsed with 1000 ml of THF
  6. customthe filtrate is evaporated to dryness
  7. dissolutionThe residue is dissolved in 75 ml of ethyl acetate at the boiling temperature, and 250 ml of n-heptane
  8. additionare slowly added
  9. temperatureAfter cooling
  10. customthe solid which has crystallised out
  11. filtrationis filtered off with suction
  12. washwashed twice with 50 ml of n-heptane each time
  13. customdried in vacuo
  14. customThe solids obtained in this way
  15. customare freed from low-boiling components and non-volatile secondary components by sublimation (p about 1×10−5 mbar, T about 170-200° C.)

출처 및 근거

ORD 기록
ord-2adaf0f840814af190edd460217d2871
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273080B2

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