Cesium carbonate → 3-Fluoro-7-methoxy-4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline

HRID 40229ノート

反応式

HRID 40229 の反応式
C(P(C(C)(C)C)C1C=CC2C(=CC=CC=2)C=1C1C2C(=CC=CC=2)C=CC=1)(C)(C)C.[C:30]1([C:36]2[CH:37]=[CH:38][C:39]3[N:40]([C:42]([CH2:45][OH:46])=[N:43][N:44]=3)[N:41]=2)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.Cl[C:48]1[C:57]2[C:52](=[CH:53][C:54]([O:58][CH3:59])=[CH:55][CH:56]=2)[N:51]=[CH:50][C:49]=1[F:60].C(=O)([O-])[O-].[Cs+].[Cs+]>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].C1(C)C=CC=CC=1>[F:60][C:49]1[CH:50]=[N:51][C:52]2[C:57]([C:48]=1[O:46][CH2:45][C:42]1[N:40]3[N:41]=[C:36]([C:30]4[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:37]=[CH:38][C:39]3=[N:44][N:43]=1)=[CH:56][CH:55]=[C:54]([O:58][CH3:59])[CH:53]=2

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 2734941(1,1'-Binaphthalen)-2-yldi-tert-butylphosphineHCID 57812703(6-Phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanolHCID 594273204-chloro-3-fluoro-7-methoxyQuinoline

生成物 1

HCID 576911383-Fluoro-7-methoxy-4-((6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methoxy)quinoline

試薬・触媒・溶媒 2

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

実験手順

A sealable tube was charged with Pd2dba3 (0.20 g, 0.22 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.18 g, 0.44 mmol), (6-phenyl-[1,2,4]triazolo[4,3-b]pyridazin-3-yl)methanol (0.100 g, 0.44 mmol), 4-chloro-3-fluoro-7-methoxyquinoline (0.14 g, 0.66 mmol), cesium carbonate (0.29 g, 0.88 mmol), and toluene and sealed. The mixture was heated at 100 C for 12 h. The mixture was allowed to cool to rt and the solid filtered, and rinsed with toluene. The solid was stirred with a mixture of EA, MeOH, CH2Cl2 and filtered. The filtrate was purified via flash chromatography using a MeOH in CH2Cl2 gradient. The resulting solid was triturated with CH2Cl2/Hexanes then purified by prep hplc. The title compound was collected as a white solid. M/Z=402.1 [M+H], calc 401.3994 for C22H16FN5O2.

後処理

  1. customsealed
  2. temperatureThe mixture was heated at 100 C for 12 h
  3. filtrationthe solid filtered
  4. washrinsed with toluene
  5. filtrationfiltered
  6. customThe filtrate was purified via flash chromatography
  7. customThe resulting solid was triturated with CH2Cl2/Hexanes
  8. customthen purified by prep hplc
  9. customThe title compound was collected as a white solid

出典と根拠

ORDレコード
ord-7e24c4995fc341a69e1db8f66cb13229
出典データセット
uspto-grants-2013_09
特許番号
US08524900B2

反応ノート

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