2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → HCID 57756249、化合物

HRID 911141

反応式

HRID 911141 の反応式
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1.[NH2:30][C:31]1[CH:51]=[CH:50][C:34]([O:35][C:36]2[C:41]([C:42]3[CH:47]=[CH:46][N:45]=[C:44]([NH:48][CH3:49])[CH:43]=3)=[CH:40][CH:39]=[CH:38][N:37]=2)=[CH:33][CH:32]=1.Cl[C:53]1[C:58]2[CH2:59][CH2:60][CH2:61][C:57]=2[C:56]([C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)=[N:55][N:54]=1.CC(C)([O-])C.[Na+]>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]>[CH3:49][NH:48][C:44]1[CH:43]=[C:42]([C:41]2[C:36]([O:35][C:34]3[CH:50]=[CH:51][C:31]([NH:30][C:53]4[N:54]=[N:55][C:56]([C:62]5[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=5)=[C:57]5[CH2:61][CH2:60][CH2:59][C:58]=45)=[CH:32][CH:33]=3)=[N:37][CH:38]=[CH:39][CH:40]=2)[CH:47]=[CH:46][N:45]=1

参加物

6

反応物 4

HCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23676156Sodium t-butoxideHCID 667351614-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amineHCID 866141641-Chloro-6,7-dihydro-4-phenyl-5H-cyclopenta[d]pyridazine

生成物 1

HCID 57756249HCID 57756249、化合物

試薬・触媒・溶媒 1

HCID 9811564Bis(dibenzylideneacetone)palladium触媒

反応条件

温度
100 °C

実験手順

A resealable reaction tube was charged with tris(dibenzylideneacetone)dipalladium (0) (0.012 g, 0.013 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (0.021 g, 0.051 mmol), 4-(2-(4-aminophenoxy)pyridin-3-yl)-N-methylpyridin-2-amine (0.075 g, 0.257 mmol), 1-chloro-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazine (0.059 g, 0.257 mmol), and sodium tert-butoxide (0.035 g, 0.359 mmol). This mixture was purged with nitrogen for several minutes, followed by addition of 0.780 mL of toluene. The vial was capped and heated at 100° C. for 1.5 h. Upon cooling, ethyl acetate was added and a precipitate formed. After filtration and washing with EtOAc, the crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column), to provide N-(4-(3-(2-(methylamino)pyridin-4-yl)pyridin-2-yloxy)phenyl)-4-phenyl-6,7-dihydro-5H-cyclopenta[d]pyridazin-1-amine as a tan solid. MS m/z=487 [M+H]+. Calc'd for C30H26N6O: 486.57.

後処理

  1. customThis mixture was purged with nitrogen for several minutes
  2. additionfollowed by addition of 0.780 mL of toluene
  3. customThe vial was capped
  4. temperatureUpon cooling
  5. additionethyl acetate was added
  6. customa precipitate formed
  7. filtrationAfter filtration
  8. washwashing with EtOAc
  9. customthe crude material was purified by ISCO silica gel chromatography (90/10/1 DCM/MeOH/NH4OH, 12 g column)

出典と根拠

ORDレコード
ord-2ce4fb20b3494e57a25d9f69d61ae3e6
出典データセット
uspto-grants-2011_09
特許番号
US08022221B2

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