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

HRID 913910노트

반응식

HRID 913910 반응식
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

참가 물질

6

반응물 2

HCID 6228DimethylformamideHCID 178506062HCID 178506062, 화합물

생성물 1

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

시약·촉매·용매 3

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

실험 절차

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)+.

후처리

  1. temperaturewas heated
  2. customcompletion of the reaction

출처 및 근거

ORD 기록
ord-1592be1ecc054d68bea558903836dc37
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026257B2

반응 노트

불러오는 중…