Oxazole → HCID 57378193、化合物

HRID 76018ノート

反応式

HRID 76018 の反応式
[Li]CCCC.[O:6]1[CH:10]=[CH:9][N:8]=[CH:7]1.[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[N:32]2[C:36]([CH3:37])=[C:35](I)[N:34]=[N:33]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]>C1COCC1.CCOC(C)=O.[Cl-].[Cl-].[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:11]([C:15]1[CH:20]=[CH:19][C:18]([S:21]([NH:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[N:32]2[C:36]([CH3:37])=[C:35]([C:7]3[O:6][CH:10]=[CH:9][N:8]=3)[N:34]=[N:33]2)(=[O:23])=[O:22])=[CH:17][CH:16]=1)([CH3:14])([CH3:13])[CH3:12]

参加物

8

反応物 3

HCID 9255OxazoleHCID 59428119HCID 59428119、化合物HCID 178418339Butyllithium

生成物 1

HCID 57378193HCID 57378193、化合物

試薬・触媒・溶媒 4

HCID 3007855Zincchloride触媒HCID 178418397HCID 178418397、化合物触媒HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a cooled (−78° C.) solution of n-BuLi (0.5 mL, 2.5 M solution in hexanes) in THF (3 mL) was added oxazole (0.1 mL, 1.5 mmol) via dropwise addition and the solution was stirred for 30 minutes. ZnCl2 solution (3.9 mL, 0.5 M in THF) was then added and the reaction mixture was warmed to room temperature and stirred an additional 2 hours. Pd(PPh3)4 (20 mg, 0.015 mmol) and 4-tert-butyl-N-[4-chloro-2-(4-iodo-5-methyl-[1,2,3]triazol-1-yl)-phenyl]-benzenesulfonamide (synthesized according to general procedure P, 77 mg, 0.15 mmol) were then added and the reaction mixture was heated at 80° C. overnight. The reaction mixture was subsequently diluted with EtOAc (25 mL) and the combined organics were washed with water (20 mL), dried (Na2SO4), and concentrated in vacuo. The crude product was purified by preparative TLC to afford the title compound: MS (ES) M+H expected 472.1, found 472.0.

後処理

  1. additionvia dropwise addition
  2. stirringstirred an additional 2 hours
  3. temperaturethe reaction mixture was heated at 80° C. overnight
  4. washthe combined organics were washed with water (20 mL)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by preparative TLC

出典と根拠

ORDレコード
ord-80cc816cf713424db11d18fd5437cf86
出典データセット
uspto-grants-2014_09
特許番号
US08835468B2

反応ノート

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