Toluene → 7-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridine

HRID 418569

Reaction equation

HRID 418569 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([Sn](CCCC)(CCCC)CCCC)[S:10][C:3]=12.Br[C:25]1[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=1.C1(C)C=CC=CC=1>>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:25]3[N:26]([CH3:30])[CH:27]=[CH:28][N:29]=3)[S:10][C:3]=12

Participants

4

Reactant 3

HCID 1140TolueneHCID 27732622-Bromo-1-methyl-1H-imidazoleHCID 575166587-Chloro-2-(tributylstannyl)thieno[3,2-b]pyridine

Product 1

HCID 221435637-chloro-2-(1-methyl-1H-imidazol-2-yl)-thieno[3,2-b]pyridineYield 94.2%

Procedure

To a solution of the tin derivative 6 (24.79 g, 54.05 mmol) and 2-bromo-1-methyl-1H-imidazole (10.4 g, 64.86 mmol) [McCallum, P. W.; Weavers, R. T.: Grimmet, M. R.; Blackman, A. G.; Aust. J. Chem.; 52; 3; 1999; 159-166.1 in toluene (180 mL) Pd[PPh3]4 (5 g, 4.32 mmol) was added and the mixture was refluxed under nitrogen for 2 days, cooled to room temperature. A precipitate was formed which was collected by filtration, washed with Et2O and dried, to afford the title compound 7 as a grey solid (12.72 g, 94% yield). MS (m/z): 250.0 (M+H).

Workup

  1. temperaturethe mixture was refluxed under nitrogen for 2 days
  2. customA precipitate was formed which
  3. filtrationwas collected by filtration
  4. washwashed with Et2O
  5. customdried

Sources & evidence

ORD record
ord-f269f90ffb4645788031a932cceb48f9
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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