Methanol → HCID 71115123, 화합물

HRID 468874노트

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HRID 468874 반응식
Cl[C:2]1[N:11]=[C:10]([C:12]2[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=2[CH3:19])[CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([NH:20][C:21]([CH:23]1[CH2:25][CH2:24]1)=[O:22])[N:6]=[CH:7]2.F[B-](F)(F)F.F[B-](F)(F)F.C1(P(C2CCCCC2)CCCP(C2CCCCC2)C2CCCCC2)CCCCC1.[C:65](=[O:68])([O-])[O-:66].[K+].[K+].[CH3:71]O>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C)C=O>[CH:23]1([C:21]([NH:20][C:5]2[CH:4]=[C:3]3[C:8]([CH:9]=[C:10]([C:12]4[CH:17]=[C:16]([F:18])[CH:15]=[CH:14][C:13]=4[CH3:19])[N:11]=[C:2]3[C:65]([O:66][CH3:71])=[O:68])=[CH:7][N:6]=2)=[O:22])[CH2:25][CH2:24]1

참가 물질

8

반응물 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 57410130HCID 57410130, 화합물HCID 71317487Phosphine, 1,1'-(1,3-propanediyl)bis[1,1-dicyclohexyl-, tetrafluoroborate(1-) (1:2)

생성물 1

HCID 71115123HCID 71115123, 화합물수율 90%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

A mixture of N-(5-chloro-7-(5-fluoro-2-methylphenyl)-2,6-naphthyridin-3-yl)cyclopropanecarboxamide (50 mg, 0.14 mmol), palladium acetate (2 mg, 0.007 mmol), 1,3-bis(dicyclohexylphosphino)propane bis(tetrafluoroborate) (9 mg, 0.014 mmol), potassium carbonate (29 mg, 0.21 mmol), methanol (0.1 mL), and N,N-dimethylformamide (1 mL) was purged with nitrogen and evacuated (3×), flushed with carbon monoxide and evacuated (2×), and then left under a carbon monoxide balloon and heated at 100° C. for 2 hours. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane) to afford the title compound as a pale yellow solid (50 mg, 90%), which was used in the next step without further purification.

후처리

  1. customwas purged with nitrogen
  2. customevacuated (3×)
  3. customflushed with carbon monoxide
  4. customevacuated (2×)
  5. waitleft under a carbon monoxide balloon
  6. customThe cooled reaction mixture
  7. washwashed with water (100 mL)
  8. customThe organic layer was separated
  9. dry with materialdried over sodium sulfate
  10. filtrationfiltered
  11. customevaporated in vacuo
  12. customto afford a residue that
  13. customwas purified by flash chromatography (silica, 4 g, ISCO, 0-50% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-b1f15aa5959542b7aead9921de09c4eb
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08623889B2

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