Triacetoxyperiodinane → Tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate

HRID 57983Notes

Reaction equation

HRID 57983 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][C:13](=[O:15])[CH2:12][N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:10][CH2:9]2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 86707089HCID 86707089, compound

Product 1

HCID 86707166Tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylateYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of tert-butyl 4-(6-bromopyridin-2-yl)-6-hydroxy-1,4-diazepane-1-carboxylate (1.05 g, 2.83 mmol) from Examples 88, 89, 148 in DCM (35 mL) at 0° C. was added (1,1,1-triacetoxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one (2.40 g, 5.66 mmol). The mixture was stirred overnight, quenched with brine (40 mL) and DCM (30 mL), and extracted with DCM (100 mL×3), and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether/ethyl acetate (5% to 50%) as eluting solvents to afford tert-butyl 4-(6-bromopyridin-2-yl)-6-oxo-1,4-diazepane-1-carboxylate as a yellow oil (846 mg, 81%). MS (ESI) m/z: 370 [M+H]+.

Workup

  1. customquenched with brine (40 mL) and DCM (30 mL)
  2. extractionextracted with DCM (100 mL×3)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography
  5. washas eluting solvents

Sources & evidence

ORD record
ord-7bace02dafde4b9795819594660b1081
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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