Ethyl orthoformate → tert-butyl 2-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetate

HRID 1502160Notes

Reaction equation

HRID 1502160 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[CH:4][C:3]=1[F:16].FC(F)(F)C(O[Si](C)(C)C)=O.[CH:28](OCC)(OCC)OCC.[N:38]([Si](C)(C)C)=[N+:39]=[N-:40]>CCOC(C)=O>[F:16][C:3]1[CH:4]=[C:5]([CH2:8][C:9]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:10])[CH:6]=[N:7][C:2]=1[N:1]1[CH:28]=[N:38][N:39]=[N:40]1

Participants

6

Reactant 4

HCID 31214Ethyl orthoformateHCID 67863Acetic acid, 2,2,2-trifluoro-, trimethylsilyl esterHCID 78378AzidotrimethylsilaneHCID 89619012Tert-butyl 2-(6-amino-5-fluoropyridin-3-yl)acetate

Product 1

HCID 89619238tert-butyl 2-(5-fluoro-6-(1H-tetrazol-1-yl)pyridin-3-yl)acetate

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To tert-butyl 2-(6-amino-5-fluoropyridin-3-yl)acetate (120 mg, 0.53 mmol) in EtOAc (2.6 mL) was added trimethylsilyl trifluoroacetate (156 μL, 0.90 mmol), triethyl orthoformate (156 μl, 0.94 mmol), and azidotrimethylsilane (112 μL, 0.85 mmol). The reaction mixture was stirred at rt overnight. The reaction mixture was concentrated to give the crude product, which was purified by column chromatography to give title compound: LC/MS: [(M+1-56-28)]+=196.4;

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customto give the crude product, which
  3. customwas purified by column chromatography

Sources & evidence

ORD record
ord-dca91d569226407289c44e0806a9fea9
Source dataset
uspto-grants-2015_12
Patent number
US09206199B2

Reaction notes

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