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

HRID 2182818

Reaction equation

HRID 2182818 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-2d04f7b6ce2b4a2baea1c6d9975d5c5f
Source dataset
uspto-grants-2005_05
Patent number
US06897319B2

Linked notes

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