Potassium Carbonate → Tert-butyl (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)piperidin-4-yl)carbamate

HRID 490298Notes

Reaction equation

[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[Cl:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>O>[C:1]([O:5][C:6](=[O:14])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:17]2[C:16]([Cl:15])=[CH:21][C:20]([C:22]([F:25])([F:23])[F:24])=[CH:19][N:18]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 120 °C

Procedure

A stirred suspension of D7 (5.5 g, 27.5 mmol), 3,6-dichloro-5-trifluoromethylpyridine (3.83 mL, 27.5 mmol) (for synthesis see Tetrahedron, 1985, 41, 4057) and potassium carbonate (11.4 g, 82.6 mmol) in dry N,N-DMF (100 mL) was heated at 120° C. for 24 h. After cooling to ambient temperature, the mixture was poured into water (1 L), stirred for 1 h and then filtered. The residue was washed with water (3×150 mL and dried (MgSO4) to afford the title compound (9.8 g).

Workup

temperatureAfter cooling to ambient temperature
filtrationfiltered
washThe residue was washed with water (3×150 mL
dry with materialdried (MgSO4)

Sources & evidence

ORD record: ord-855bff68ee5b4c99a0fe01f282118e39
Source dataset: uspto-grants-2009_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07528151B2

Reaction notes

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