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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
Notes
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Reaction equation

HRID 2193749 reaction equation
[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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-61076359863843aab06d714b3bfd8b9a
Source dataset
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08329726B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes