Azidotrimethylsilane → HCID 178497451, compound

HRID 415948Notes

Reaction equation

HRID 415948 reaction equation
[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2([C:16]#[N:17])[CH2:15][CH2:14][O:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.C[Si]([N:23]=[N+:24]=[N-:25])(C)C>COCCOC>[CH3:1][O:2][C:3](=[O:18])[C:4]1[CH:5]=[CH:6][C:7]([C:10]2([C:16]3[NH:25][N:24]=[N:23][N:17]=3)[CH2:11][CH2:12][O:13][CH2:14][CH2:15]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 666188074-(4-Cyano-tetrahydro-pyran-4-yl)-benzoic acid methyl ester

Product 1

HCID 178497451HCID 178497451, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

A solution of 4-(4-cyano-tetrahydro-pyran-4-yl)-benzoic acid methyl ester (400 mg, 1.63 mmol), trimethylsilyl azide (TMSN3) (40 mg, 2.1 eq), and Bu2Sn(O) (40 mg, 1.0 eq) in DME was heated in the microwave at 150° C. for 4 hours. After the reaction was done the mixture was washed with water and extracted with EtOAc. The organic phase was dried and evaporated to give 4-[4-(1H-tetrazol-5-yl)-tetrahydro-pyran-4-yl]-benzoic acid methyl ester.

Workup

  1. washwas washed with water
  2. extractionextracted with EtOAc
  3. customThe organic phase was dried
  4. customevaporated

Sources & evidence

ORD record
ord-9937ee4ac93842fbb104ae206795ae50
Source dataset
uspto-grants-2012_01
Patent number
US08088771B2

Reaction notes

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