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

HRID 573550Notes

Reaction equation

HRID 573550 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.C1(OC2C=CC=CC=2)C=CC=CC=1>>[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

3

Reactant 2

HCID 7583Diphenyl EtherHCID 683238684-Amino-2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 683240582-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amineYield 61.9%

Procedure

Alternatively, 4-amino-2-bromo-6-methyl-3-[3-(methyloxy)-phenyl]thieno-[2,3-b]pyridine-5-carboxylic acid (856 mg, 2.177 mmol) (Description 16) in diphenyl ether (8 mL, 50.3 mmol) was heated at 200° C. for 4.5 h and stand at RT overnight for 16 h. The mixture was purified by chromatography on silica gel, eluting with a gradient of 0-100% ethyl acetate in cyclohexane, to give the title compound (471 mg).

Workup

  1. customThe mixture was purified by chromatography on silica gel
  2. washeluting with a gradient of 0-100% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-6d5f45cc50e044cb962bc3d19e84bcc3
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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