Hydrochloric Acid → 2-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehyde

HRID 84362Notes

Reaction equation

HRID 84362 reaction equation
C[O:2][CH:3](OC)[C:4]1[N:8]([CH3:9])[C:7]([C:10]2[S:18][C:17]3[C:12](=[N:13][CH:14]=[CH:15][C:16]=3[O:19][C:20]3[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][C:21]=3[F:29])[CH:11]=2)=[N:6][CH:5]=1.Cl>CC(C)=O.O>[F:29][C:21]1[CH:22]=[C:23]([N+:26]([O-:28])=[O:27])[CH:24]=[CH:25][C:20]=1[O:19][C:16]1[CH:15]=[CH:14][N:13]=[C:12]2[CH:11]=[C:10]([C:7]3[N:8]([CH3:9])[C:4]([CH:3]=[O:2])=[CH:5][N:6]=3)[S:18][C:17]=12

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 579195802-(5-(Dimethoxymethyl)-1-methyl-1H-imidazol-2-yl)-7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridine

Product 1

HCID 579195642-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)-1-methyl-1H-imidazole-5-carbaldehydeYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution 42 (1.8 g, 4.05 mmol) in acetone (100 mL) and water (100 mL) was added diluted HCl (20 mL, 2M, 40.0 mmol) and the reaction mixture was stirred at RT overnight. It was then concentrated to dryness. The residual solid was dissolved in DCM, washed with water, dried over Na2SO4, filtered and concentrated. The resultant solid was triturated with Et2O to afford 43 (1.3 g, 81% yield), which used without additional purification. MS (m/z): 399.2 (M+H).

Workup

  1. concentrationIt was then concentrated to dryness
  2. dissolutionThe residual solid was dissolved in DCM
  3. washwashed with water
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resultant solid was triturated with Et2O

Sources & evidence

ORD record
ord-14f5e6cbe1ac4b989ec226cf66b8ad7c
Source dataset
uspto-grants-2014_09
Patent number
US08846927B2

Reaction notes

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