Quinoline → 2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

HRID 573549Notes

Reaction equation

[NH2:1][C:2]1[C:7](C(O)=O)=[C:6]([CH3:11])[N:5]=[C:4]2[S:12][C:13]([Br:23])=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=3)[C:3]=12.N1C2C(=CC=CC=2)C=CC=1>[Cu]>[Br:23][C:13]1[S:12][C:4]2[N:5]=[C:6]([CH3:11])[CH:7]=[C:2]([NH2:1])[C:3]=2[C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A mixture of 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid (400 mg, 1.017 mmol) (Description 16), copper (194 mg, 3.05 mmol) and quinoline (3 mL, 25.3 mmol) was heated in a microwave at 180° C. for 30 min and then 190° C. for 30 min. After cooling to RT, the mixture was purified by chromatography on silica gel, eluting with a gradient of 40-60% ethyl acetate in cyclohexane, to give the title compound (214 mg). LCMS (A) m/z: 349/351 [M+1]+, Rt 1.08 min (acidic).

Workup

temperatureAfter cooling to RT
customthe mixture was purified by chromatography on silica gel
washeluting with a gradient of 40-60% ethyl acetate in cyclohexane

Sources & evidence

ORD record: ord-83200aecb0384ab2b49f9394b28c7c20
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

Loading…