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

HRID 1026792Notes

Reaction equation

HRID 1026792 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-cdbd2f7bb29a465f8f39bfb56ed68c74
Source dataset
uspto-grants-2014_05
Patent number
US08729268B2

Reaction notes

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