Dimethylformamide → 1H-Benzimidazole-7-carbonitrile, 5-(trifluoromethyl)-

HRID 913910ノート

反応式

HRID 913910 の反応式
Br[C:2]1[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=[C:4]([C:11]([F:14])([F:13])[F:12])[CH:3]=1.[CH3:15][N:16](C)C=O>O.[C-]#N.[Zn+2].[C-]#N.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:12][C:11]([F:14])([F:13])[C:4]1[CH:3]=[C:2]([C:15]#[N:16])[C:7]2[NH:8][CH:9]=[N:10][C:6]=2[CH:5]=1

参加物

6

反応物 2

HCID 6228DimethylformamideHCID 178506062HCID 178506062、化合物

生成物 1

HCID 1785098911H-Benzimidazole-7-carbonitrile, 5-(trifluoromethyl)-収率 45%

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 44119782Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒

実験手順

A red suspension of 7-Bromo-5-(trifluoromethyl)-1H-benzo[d]imidazole (270 mg, 1.02 mmol), zinc cyanide (1.12 mmol), and PdCl2(dppf) (0.06 mmol) in Water (3 ml) and dimethylformamide (10 ml) was heated with stirring under argon for 2 h. At the end, LC-MS analysis revealed completion of the reaction. The reaction mixture was cooled to ambient temperature and was subjected to preparative HPLC (8 injections using HPLC method 14). Fractions containing the required product were combined and evaporated in vacuo to give 97 mg (45% yield). 1H NMR (CD3OD, 500 MHz) δ 7.88 (s, 1H), 8.21 (s, 1H), 8.54 (s, 1H); IR (KBr) 2229 (CN stretching); LC/MS (HPLC method 9): tR=1.8 min, 212(MH)+.

後処理

  1. temperaturewas heated
  2. customcompletion of the reaction

出典と根拠

ORDレコード
ord-1592be1ecc054d68bea558903836dc37
出典データセット
uspto-grants-2011_09
特許番号
US08026257B2

反応ノート

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