Water → (4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone

HRID 2182818

반응식

HRID 2182818 반응식
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([C:35]([C:37]2[N:41]([CH3:42])[CH:40]=[C:39]([CH:43]=[O:44])[CH:38]=2)=[O:36])=[CH:33][CH:32]=1.O>C(Cl)Cl.CCOCC>[Cl:30][C:31]1[CH:46]=[CH:45][C:34]([C:35]([C:37]2[N:41]([CH3:42])[CH:40]=[C:39]([CH:43]([OH:44])[C:2]3[N:3]=[CH:4][N:5]([C:7]([C:8]4[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=4)([C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)[C:14]4[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:6]=3)[CH:38]=2)=[O:36])=[CH:33][CH:32]=1

참가 물질

7

반응물 4

HCID 962WaterHCID 6182524-Iodo-1-tritylimidazoleHCID 224810525-(4-Chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehydeHCID 178418443HCID 178418443, 화합물

생성물 1

HCID 22481044(4-chloro-phenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2-yl}methanone수율 138.9%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6344Dichloromethane용매2회

실험 절차

To 4.4 g (0.01 mole) 4-iodo-1-tritylimidazole in 80 mL of CH2Cl2 was added dropwise 3.3 mL of 3.0 M ethylmagnesium bromide in Et2O. After stirring for 1 h, a solution of 1.0 g (0.004 mole) of 5-(4-chlorobenzoyl)-1-methyl-1H-pyrrole-3-carboxaldehyde in 10 mL of CH2Cl2 was added dropwise. The resulting reaction mixture was stirred for 2.5 h after which it was poured into water. The solid was filtered off through celite. The organics from the filtrate were separated off, washed with water, brine and dried (Na2SO4). The solvent was evaporated in vacuo to give 3.1 g of (4-chlorophenyl)-{4-[hydroxy-(1-trityl-1H-imidazol-4-yl)-methyl]-1-methyl-1H-pyrrol-2yl}-methanone: CI-MS m/z=559 (M++H). 1HNMR (CDCl3) δ 7.7 (m, 5H) 7.4-7.0 (m, 16H); 6.5 (m, 1H); 3.75 (s, 3H).

후처리

  1. customThe resulting reaction mixture
  2. stirringwas stirred for 2.5 h after which it
  3. filtrationThe solid was filtered off through celite
  4. customThe organics from the filtrate were separated off
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated in vacuo

출처 및 근거

ORD 기록
ord-2d04f7b6ce2b4a2baea1c6d9975d5c5f
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06897319B2

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