Potassium Carbonate → 7-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

HRID 1423846Notes

Reaction equation

HRID 1423846 reaction equation
[Br:1][C:2]1[CH:7]=[C:6](F)[C:5]([N+:9]([O-:11])=[O:10])=[CH:4][C:3]=1[Cl:12].[NH2:13][CH2:14][CH:15]1[CH2:30][CH2:29][CH2:28][C:17]2([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH2:18]2)[CH2:16]1.C(=O)([O-])[O-].[K+].[K+]>CC#N>[Br:1][C:2]1[C:3]([Cl:12])=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH:13][CH2:14][CH:15]2[CH2:30][CH2:29][CH2:28][C:17]3([O:21][C:20](=[O:22])[N:19]([CH2:23][C:24]([CH3:26])([CH3:27])[CH3:25])[CH2:18]3)[CH2:16]2)[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 104001051-Bromo-2-chloro-5-fluoro-4-nitrobenzeneHCID 711160567-(Aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one

Product 1

HCID 711160457-(((5-Bromo-4-chloro-2-nitrophenyl)amino)methyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-oneYield 44.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A rt suspension of 1-bromo-2-chloro-5-fluoro-4-nitrobenzene (0.600 g, 2.36 mmol) in MeCN (8 mL) was treated with 7-(aminomethyl)-3-neopentyl-1-oxa-3-azaspiro[4.5]decan-2-one (0.400 g, 1.57 mmol) and potassium carbonate (0.543 g, 3.93 mmol). The reaction was stirred for 18 h, and the solids were filtered off and washed with EtOAc. The filtrate was concentrated and purified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection) to provide the title compound (0.340 g, 44% yield) as an orange solid. MS (m/z) 488.1, 490.1 (M+H+).

Workup

  1. filtrationthe solids were filtered off
  2. washwashed with EtOAc
  3. concentrationThe filtrate was concentrated
  4. custompurified on a 40 g silica gel column (0-100% DCM/hexanes, 20 min gradient; 100% DCM, 15 min; 40 mL/min elution; 254 nm detection)

Sources & evidence

ORD record
ord-55a0e8fc57a746bf90ed4f2b1bb84814
Source dataset
uspto-grants-2015_01
Patent number
US08927585B2

Reaction notes

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