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Ethylenediaminetetraacetic Acid → (7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)methanone

HRID 2193749
ノート
印刷プレビュー

反応式

HRID 2193749 の反応式
[Si:1]([O:8][CH:9]1[CH2:12][N:11]([C:13]([C:15]2[S:23][C:22]3[C:17](=[N:18][CH:19]=[CH:20][C:21]=3[O:24][C:25]3[CH:30]=[CH:29][C:28]([N+:31]([O-])=O)=[CH:27][C:26]=3[F:34])[CH:16]=2)=[O:14])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>CO.C1COCC1>[NH2:31][C:28]1[CH:29]=[CH:30][C:25]([O:24][C:21]2[CH:20]=[CH:19][N:18]=[C:17]3[CH:16]=[C:15]([C:13]([N:11]4[CH2:12][CH:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2])[CH2:10]4)=[O:14])[S:23][C:22]=23)=[C:26]([F:34])[CH:27]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6049Ethylenediaminetetraacetic AcidHCID 4311764Sodium borohydrideHCID 58790045(3-(tert-Butyldimethylsilyloxy)azetidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone

生成物 1

HCID 58790300(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)(3-(tert-butyldimethylsilyloxy)azetidin-1-yl)methanone収率 46%

試薬・触媒・溶媒 1

HCID 21899815
MeOH tetrahydrofuran
溶媒

実験手順

To a solution of (3-(tert-butyldimethylsilyloxy)azetidin-1-yl)(7-(2-fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)methanone 273 (336 mg, 0.67 mmol) and NiCl2.6H2O (318 g, 1.34 mmol) in MeOH/THF (4.7 mL/4.7 mL) was added NaBH4 (101 g, 2.68 mmol) at 0° C. and the mixture stirred for 1 hr. The reaction mixture was added to an EDTA.4Na (1.1 g/100 mL) solution and extracted with EtOAc. The aqueous layer was filtered and extracted again with EtOAc. The combined organic phase was dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography (pure EtOAc) giving 274 as creamy foam (145.2 mg, 46% yield). MS (m/z): (M+1) 474.1 (100%).

後処理

  1. extraction4Na (1.1 g/100 mL) solution and extracted with EtOAc
  2. filtrationThe aqueous layer was filtered
  3. extractionextracted again with EtOAc
  4. dry with materialThe combined organic phase was dried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography (pure EtOAc)

出典と根拠

ORDレコード
ord-61076359863843aab06d714b3bfd8b9a
出典データセット
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08329726B2

反応ノート

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