1H-1,2,4-Triazole → [1-(5-[1,2,4]Triazol-1-yl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester

HRID 2038786Notes

Reaction equation

[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14](I)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[NH:19]1[CH:23]=[N:22][CH:21]=[N:20]1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CN[C@@H]1CCCC[C@H]1NC>O.CCOC(C)=O.[Cu]I.CN(C=O)C>[C:1]([O:5][C:6](=[O:18])[NH:7][C:8]1([C:11]2[CH:16]=[CH:15][C:14]([N:19]3[CH:23]=[N:22][CH:21]=[N:20]3)=[CH:13][N:12]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

[1-(5-Iodo-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (100 mg, 0.28 mmol), CuI (11 mg, 0.06 mmol), 1,2,4-triazole (29 mg, 0.42 mmol) and K3PO4 (118 mg, 0.556 mmol) were mixed in a 8-mL microwave vial. (1R,2R)-N,N′-dimethyl-cyclohexane-1,2-diamine (18 μL, 0.11 mmol) was added to the mixture under argon followed by DMF (2 mL). The reaction was heated at 100° C. overnight. The reaction was then cooled to room temperature and diluted with water (50 mL) and EtOAc (50 mL). The organic layer was collected and dried over MgSO4. The residue was purified by flash chromatography on silica gel (20% EtOAc/Hex to 100% EtOAc) to give [1-(5-[1,2,4]triazol-1-yl-pyridin-2-yl)-cyclopropyl]-carbamic acid tert-butyl ester (40 mg, 0.13 mmol, 48%) as a semi-solid.

Workup

temperatureThe reaction was then cooled to room temperature
customThe organic layer was collected
dry with materialdried over MgSO4
customThe residue was purified by flash chromatography on silica gel (20% EtOAc/Hex to 100% EtOAc)

Sources & evidence

ORD record: ord-281fdd9445b04763acae5da1f2034a2b
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08575360B2

Reaction notes

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