Cesium carbonate → 4-[5-(5-Bromo-pyridin-3-yl)-tetrazol-2-ylmethyl]-benzoic acid tert-butyl ester

HRID 349461Notes

Reaction equation

HRID 349461 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([C:8]2[N:9]=[N:10][NH:11][N:12]=2)[CH:7]=1.[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:24]=[CH:23][C:22]([CH2:25]Br)=[CH:21][CH:20]=1)([CH3:16])([CH3:15])[CH3:14].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O>[C:13]([O:17][C:18](=[O:27])[C:19]1[CH:20]=[CH:21][C:22]([CH2:25][N:10]2[N:11]=[N:12][C:8]([C:6]3[CH:5]=[N:4][CH:3]=[C:2]([Br:1])[CH:7]=3)=[N:9]2)=[CH:23][CH:24]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 41737615-(5-Bromo-3-pyridyl)-1H-tetrazoleHCID 11414578Tert-butyl 4-(bromomethyl)benzoate

Product 1

HCID 689789854-[5-(5-Bromo-pyridin-3-yl)-tetrazol-2-ylmethyl]-benzoic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The tetrazole (27.3 g, 104 mmol) from Step (a) was treated with 4-bromomethyl-benzoic acid tert-butyl ester (31.0 g, 114 mmol) and cesium carbonate (74.3 g, 228 mmol) in dimethylformamide (400 mL) at room temperature for 5.5 hours. The solvent was evaporated in vacuo and the residue passed through a pad of silica gel eluting with CH2Cl2:THF 19:1, to give a 9:1 mixture of regioisomers (40.07 g, 93%). 1H NMR (DMSO-d6) δ 9.16 (s, 1H), 8.87 (s, 1H), 8.54 (s, 1H), 7.91 (d, J=8 Hz, 2H), 7.51 (d, J=9 Hz, 2H), 6.13 (s, 2H), 1.57 (s, 9H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customto give
  3. additiona 9:1 mixture of regioisomers (40.07 g, 93%)

Sources & evidence

ORD record
ord-f5ff92bcc80d49e7bd4fbd4eb7ba6ff4
Source dataset
uspto-grants-2007_02
Patent number
US07179822B2

Reaction notes

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