Sodium Carbonate → 6-(3-Fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

HRID 1846938ノート

反応式

HRID 1846938 の反応式
[F:1][C:2]([F:16])([F:15])[C:3]1[N:7]2[CH:8]=[C:9](B(O)O)[CH:10]=[CH:11][C:6]2=[N:5][N:4]=1.Br[C:18]1[CH:23]=[CH:22][C:21]([O:24][C:25]([F:28])([F:27])[F:26])=[C:20]([F:29])[CH:19]=1.C([O-])([O-])=O.[Na+].[Na+]>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.CN(C=O)C>[F:29][C:20]1[CH:19]=[C:18]([C:9]2[CH:10]=[CH:11][C:6]3[N:7]([C:3]([C:2]([F:16])([F:15])[F:1])=[N:4][N:5]=3)[CH:8]=2)[CH:23]=[CH:22][C:21]=1[O:24][C:25]([F:26])([F:27])[F:28]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 27822174-Bromo-2-fluoro-1-(trifluoromethoxy)benzeneHCID 581189153-(Trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid

生成物 1

HCID 866502296-(3-Fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridin-6-ylboronic acid (56.2 mg, 0.217 mmol), 4-bromo-2-fluoro-1-(trifluoromethoxy)benzene (50.0 mg, 0.217 mmol, 1.0 equiv.) and Pd(PPh3)4 (12.6 mg, 0.0109 mmol, 0.05 equiv.) was placed in a 50 mL round bottomed flask under a nitrogen atmosphere. To the flask were added 2M-Na2CO3 (1.0 mL, 2.0 mmol) and DMF (4 mL) subsequently at ambient temperature. The mixture was heated at 110° C. for 1 hours. The mixture was filtered through Celite (3 g) and the Celite was washed with EtOAc (70 mL). The organic layer was washed with brine (30 mL) and dried with Na2SO4. The solvent was removed under a reduced pressure. Obtained crude mixture was purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:3 to 1:1, Rf=0.3 with EtOAc/hexane=1:1) to give 6-(3-fluoro-4-(trifluoromethoxy)phenyl)-3-(trifluoromethyl)-[1,2,4]triazolo[4,3-a]pyridine as colorless crystals

後処理

  1. filtrationThe mixture was filtered through Celite (3 g)
  2. washthe Celite was washed with EtOAc (70 mL)
  3. washThe organic layer was washed with brine (30 mL)
  4. dry with materialdried with Na2SO4
  5. customThe solvent was removed under a reduced pressure
  6. customObtained crude mixture
  7. customwas purified by a column chromatography (SiO2=25 g, EtOAc/hexane=1:3 to 1:1, Rf=0.3 with EtOAc/hexane=1:1)

出典と根拠

ORDレコード
ord-7572b9b7f68c4feb9f92da459540676e
出典データセット
uspto-grants-2015_02
特許番号
US08952034B2

反応ノート

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