Oxazole → Oxazole thiazole indole

HRID 14343

反応式

HRID 14343 の反応式
[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[CH2:11]([Li])[CH2:12][CH2:13][CH3:14]>[Cl-].[Zn+2].[Cl-].C1COCC1>[O:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[NH:8]1[C:9]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:2]=[CH:7]1.[S:6]1[CH:10]=[CH:9][N:8]=[CH:7]1

参加物

6

反応物 3

HCID 9255OxazoleHCID 9256ThiazoleHCID 178418339Butyllithium

生成物 1

HCID 86594208Oxazole thiazole indole

試薬・触媒・溶媒 2

HCID 3007855Zincchloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

Alternatively, iodo indole 5 is reacted with an alkyl halide, for example as propyl or butyl iodide, bromide, or chloride in the presence of a base, for example sodium hydride or potassium tert-butoxide, more preferably potassium tert-butoxide, in an organic solvent, for example THF, DMF or DMSO, preferably DMSO, at a temperature from room temperature to about 100° C., to yield iodo alkyl 9. An Oxazole or a thiazole in an organic solvent, for example dialkyl ether or THF, at a temperature from about 0 to about −78° C. is reacted with a base, preferably butyl lithium and optionally left stirring for from about 15 to about 60 min. Zinc chloride is then added and the mixture is allowed to warm to 0-30° C., at which time iodo alkyl 9 is added, followed by tetrakis triphenylphosphine palladium. The mixture is then optionally left stirring at a temperature from room temperature to about 80° C. to yield oxazole/thiazole indole 10.The hydrolysis of 10 by methods known to those skilled in the art yields oxazole/thiazole acid 11. Oxazole/thiazole acid 11 is coupled to amine (VIII) using methods known to those skilled in the art.

後処理

  1. customfrom about 0 to about −78° C.
  2. waitoptionally left
  3. additionis added
  4. waitThe mixture is then optionally left
  5. stirringstirring at a temperature from room temperature to about 80° C.

出典と根拠

ORDレコード
ord-9347fa71c7034c56a09f02b9893039a7
出典データセット
uspto-grants-2010_06
特許番号
US07727997B2

関連ノート

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