Di-tert-butyl dicarbonate → Tert-butyl 4-(6-bromo-3-methoxy-2-pyridyl)-6-hydroxy-1,4-diazepane-1-carboxylate

HRID 57909Notes

Reaction equation

HRID 57909 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]([OH:15])[CH2:12][NH:11][CH2:10][CH2:9]2)[C:5]([O:16][CH3:17])=[CH:4][CH:3]=1.C(=O)(OC(C)(C)C)[O:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=O.C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:14][CH:13]([OH:15])[CH2:12][N:11]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:19])[CH2:10][CH2:9]2)[C:5]([O:16][CH3:17])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 90495Di-tert-butyl dicarbonateHCID 516892Sodium BicarbonateHCID 867071001-(6-Bromo-3-methoxy-2-pyridyl)-1,4-diazepan-6-ol

Product 1

HCID 86707101Tert-butyl 4-(6-bromo-3-methoxy-2-pyridyl)-6-hydroxy-1,4-diazepane-1-carboxylateYield 65.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-(6-bromo-3-methoxy-2-pyridyl)-1,4-diazepan-6-ol (0.9968 mmol; 301.2 mg), tert-butoxycarbonyl tert-butyl carbonate (1.495 mmol; 326.3 mg), and sodium bicarbonate (9.968 mmol; 837.4 mg) in dichloromethane (20 Ml) was stirred at room temperature overnight. The mixture was concentrated, and the residue was purified on silica eluted with 0 to 40% EtOAc in DCM to afford tert-butyl 4-(6-bromo-3-methoxy-2-pyridyl)-6-hydroxy-1,4-diazepane-1-carboxylate (262.5 mg, 65%).

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified on silica
  3. washeluted with 0 to 40% EtOAc in DCM

Sources & evidence

ORD record
ord-65c34ea774bc487abdf2df1463c31a64
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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