反応式
COC(=O)C1C=CC(C)=C(Br)C=1.BrC1C=C(C#N)C=CC=1C.[C:23]([C:25]1[CH:26]=[CH:27][C:28]([CH3:48])=[C:29]([C:31]2[CH:36]=[CH:35][C:34]([NH:37][C:38](=[O:47])[C:39]3[C:44]([F:45])=[CH:43][CH:42]=[CH:41][C:40]=3[F:46])=[CH:33][CH:32]=2)[CH:30]=1)#[N:24].[N-:49]=[N+:50]=[N-:51].[Na+].[Cl-].[NH4+]>CN(C=O)C.CCOC(C)=O>[C:23]([C:25]1[CH:26]=[CH:27][C:28]([CH3:48])=[C:29]([C:31]2[CH:32]=[CH:33][C:34]([NH:37][C:38](=[O:47])[C:39]3[C:40]([F:46])=[CH:41][CH:42]=[CH:43][C:44]=3[F:45])=[CH:35][CH:36]=2)[CH:30]=1)#[N:24].[F:46][C:40]1[CH:41]=[CH:42][CH:43]=[C:44]([F:45])[C:39]=1[C:38]([NH:37][C:34]1[CH:33]=[CH:32][C:31]([C:29]2[CH:30]=[C:25]([C:23]3[NH:51][N:50]=[N:49][N:24]=3)[CH:26]=[CH:27][C:28]=2[CH3:48])=[CH:36][CH:35]=1)=[O:47]参加物
反応物 5
生成物 2
試薬・触媒・溶媒 2
反応条件
- 温度
- 120 °C
実験手順
N-(5′-cyano-2′-methyl-biphenyl-4-yl)-2,6-difluoro-benzamide (Compound A) was prepared by an analogous method as Compound 1 except that 3-bromo-4-methyl-benzoic acid methyl ester was replaced with 2-bromo-4-cyano-toluene. A mixture of Compound A (348 mg 1 mmol), sodium azide (78 mg 1.2 mmol), and ammonium chloride (65 mg, 1.2 mmol) in DMF (5 ml) was stirred and heated at 120° C. for 10 hr. After cooling the reaction mixture to room temperature, EtOAc (200 ml) was added, and the mixture was washed with water (60 ml×3). The EtOAc layer was concentrated and the residue was subjected to silica gel chromatography (Hexanes:EtOAc, EtOAc:MeOH) to give the product, 2,6-difluoro-N-[2′-methyl-5′-(1H-tetrazol-5-yl)-biphenyl-4-yl]-benzamide (313 mg, yield 80%) as a off-white solid.
後処理
- temperatureAfter cooling the reaction mixture to room temperature
- washthe mixture was washed with water (60 ml×3)
- concentrationThe EtOAc layer was concentrated
出典と根拠
- ORDレコード
- ord-5c733a6bc4d941c9b7c158ae3b816816
- 出典データセット
- uspto-grants-2013_11
- 特許番号
- US08592486B2
関連ノート
読み込み中…