Potassium Phosphate, Tribasic → HCID 45269229、化合物

HRID 659710ノート

反応式

HRID 659710 の反応式
[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

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 28390692HCID 28390692、化合物HCID 57708073HCID 57708073、化合物HCID 67346612HCID 67346612、化合物

生成物 1

HCID 45269229HCID 45269229、化合物

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
110 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f719707ac19445f49e9ae54825c4dd71
出典データセット
uspto-grants-2011_12
特許番号
US08080546B2

反応ノート

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