4-Iodo-1-tritylimidazole → benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone

HRID 1174666Notes

Reaction equation

HRID 1174666 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.CON(C)[C:33]([C:35]1[C:40]2=[N:41][S:42][N:43]=[C:39]2[CH:38]=[CH:37][CH:36]=1)=[O:34]>ClCCl>[N:43]1[S:42][N:41]=[C:40]2[C:35]([C:33]([C:2]3[N:3]=[CH:4][N:5]([C:7]([C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=4)([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[CH:6]=3)=[O:34])=[CH:36][CH:37]=[CH:38][C:39]=12

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 59749564Benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amideHCID 178418443HCID 178418443, compound

Product 1

HCID 59749576benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-iodo-1-tritylimidazole (commercially available from Synchem) (6.3 g, 14.4 mmol) in dichloromethane (100 mL) at rt was treated with ethyl magnesium bromide (4.8 mL, 14.4 mmol, 3M in THF) and allowed to react for 1 h. A solution of benzo[1,2,5]thiadiazole-4-carboxylic acid methoxy-methyl-amide (Intermediate L2) (2.0 g, 9.0 mmol) in dichloromethane (50 mL) was added via syringe at rt and stirred for 40 m. The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 30% EtOAc:hexane to give benzo[1,2,5]thiadiazol-4-yl-(1-trityl-1H-imidazol-4-yl)-methanone (Intermediate L3), 1 g (25%).

Workup

  1. customto react for 1 h
  2. customThe residue was isolated in a typical aqueous workup
  3. custompurified by chromatography on silica gel with 30% EtOAc

Sources & evidence

ORD record
ord-2ca5ddb4ab8e45c4ad2f37b91991ed8c
Source dataset
uspto-grants-2010_11
Patent number
US07838545B2

Reaction notes

Loading…