(R)-(3-(Dimethylamino)pyrrolidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone → (R)-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(3-(dimethylamino) pyrrolidin-1-yl)methanone

HRID 418586

Reaction equation

HRID 418586 reaction equation
[CH3:1][N:2]([CH3:30])[C@@H:3]1[CH2:7][CH2:6][N:5]([C:8]([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-])=O)=[CH:22][C:21]=3[F:29])[CH:11]=2)=[O:9])[CH2:4]1>CC(O)=O.Cl.[Fe]>[NH2:26][C:23]1[CH:24]=[CH:25][C:20]([O:19][C:16]2[CH:15]=[CH:14][N:13]=[C:12]3[CH:11]=[C:10]([C:8]([N:5]4[CH2:6][CH2:7][C@@H:3]([N:2]([CH3:30])[CH3:1])[CH2:4]4)=[O:9])[S:18][C:17]=23)=[C:21]([F:29])[CH:22]=1

Participants

5

Reactant 1

HCID 58790264(R)-(3-(Dimethylamino)pyrrolidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone

Product 1

HCID 58790294(R)-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(3-(dimethylamino) pyrrolidin-1-yl)methanoneYield 77%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of the nitro compound 25 (708 mg, 1.64 mmol) in AcOH (16 mL) at 90° C., was added iron powder (928 mg, 16.6 mmol) and the reaction mixture was stirred vigorously for 20 min. The grey suspension was dissolved in 1N HCl (50 mL) and washed with CHCl3 (50 mL). The aqueous phase was basified with NH4OH to pH-10, extracted with CHCl3. The organic phase was collected, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the title compound 26 (506 mg, 77%) as a white solid. MS (m/z): 401.1 (M+H).

Workup

  1. washwashed with CHCl3 (50 mL)
  2. extractionextracted with CHCl3
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-52225458db804a0e9140c41fe527c3a6
Source dataset
uspto-grants-2012_01
Patent number
US08093264B2

Linked notes

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