Potassium Phosphate, Tribasic → HCID 45269229, 화합물

HRID 659710노트

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HRID 659710 반응식
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH:9]1([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([OH:21])[CH:15]=2)[CH2:11][CH2:10]1.C(P(C(C)(C)C)C1C=CC=CC=1C1C(CCC)=CC(CCC)=CC=1CCC)(C)(C)C.Cl[C:54]1[C:55]2[CH:64]=[N:63][N:62]([C:65]3[CH:70]=[CH:69][CH:68]=[C:67]([F:71])[CH:66]=3)[C:56]=2[N:57]([CH3:61])[C:58](=[O:60])[CH:59]=1>C1COCC1.C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:9]1([NH:12][C:13](=[O:22])[C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([O:21][C:54]3[C:55]4[CH:64]=[N:63][N:62]([C:65]5[CH:70]=[CH:69][CH:68]=[C:67]([F:71])[CH:66]=5)[C:56]=4[N:57]([CH3:61])[C:58](=[O:60])[CH:59]=3)[CH:15]=2)[CH2:10][CH2:11]1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 28390692HCID 28390692, 화합물HCID 57708073HCID 57708073, 화합물HCID 67346612HCID 67346612, 화합물

생성물 1

HCID 45269229HCID 45269229, 화합물

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
110 °C

실험 절차

In sealed a glass tube, a mixture of potassium phosphate tribasic (251 mg, 1.18 mmol), tris(dibenzylideneacetone)dipalladium (0) (14 mg, 0.015 mmol), N-cyclopropyl-3-hydroxy-4-methylbenzamide (136 mg, 0.71 mmol), 2-di-t-butylphosphino-2′,4′,6′-tri-1-propyl-1,1′-biphenyl (14 mg, 0.032 mmol) and 4-chloro-1-(3-fluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (164 mg, 0.59 mmol) in THF (0.5 mL) and toluene (1.30 mL) was heated at 110° C. in an oil bath for 18 h. The reaction mixture was cooled to RT, quenched with saturated ammonium chloride, and extracted twice with EtOAc. The combined EtOAc layers were washed with brine, dried and concentrated. The resulting crude material was purified on an ISCO (12 g column) eluting with a solvent gradient of 50-90% EtOAc in hexanes, to afford the title compound as a tan amorphous solid. MS (ESI, pos.ion) m/z: 433.0 (M+1).

후처리

  1. customIn sealed a glass tube
  2. temperatureThe reaction mixture was cooled to RT
  3. customquenched with saturated ammonium chloride
  4. extractionextracted twice with EtOAc
  5. washThe combined EtOAc layers were washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customThe resulting crude material was purified on an ISCO (12 g column)
  9. washeluting with a solvent gradient of 50-90% EtOAc in hexanes

출처 및 근거

ORD 기록
ord-f719707ac19445f49e9ae54825c4dd71
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08080546B2

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