Cyclohexylamine → 6-chloro-N-cyclohexyl-4-iodopyridin-2-amine

HRID 390098Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]1([NH2:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>C(OCC)(=O)C>[Cl:9][C:4]1[N:3]=[C:2]([NH:16][CH:10]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]2)[CH:7]=[C:6]([I:8])[CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of 2,6-dichloro-4-iodopyridine (5 g, 18.3 mmol) and cyclohexylamine (18.1 g, 183 mmol) was heated in a Biotage Initiator microwave at 150° C. for 30 min. Ethyl acetate (150 mL) was added and the mixture washed with water (100 mL) and brine (50 mL). The organics were concentrated and the residual oil purified by flash chromatography on silica gel eluting with 10% ethyl acetate in hexanes to provide the title compound. Yield: 4.7 g (76%). MS (DCI/NH3) m/z 337 (M+H)+.

Workup

washthe mixture washed with water (100 mL) and brine (50 mL)
concentrationThe organics were concentrated
customthe residual oil purified by flash chromatography on silica gel eluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-531c5dfd3de242e0991ad3f67dcb579a
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08383624B2

Reaction notes

Loading…