(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 2193659ノート

反応式

HRID 2193659 の反応式
[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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 313Hydrochloric Acid溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8790aa6cb2134530a96f27b4fcaff69b
出典データセット
uspto-grants-2012_12
特許番号
US08329726B2

反応ノート

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