Diphenyl Ether → HCID 68323876, compound

HRID 573571Notes

Reaction equation

HRID 573571 reaction equation
C1(OC2C=CC=CC=2)C=CC=CC=1.[NH2:14][C:15]1[C:20](C(O)=O)=[C:19]([CH3:24])[N:18]=[C:17]2[S:25][C:26]([Br:35])=[C:27]([C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=3)[C:16]=12>C(Cl)Cl>[Br:35][C:26]1[S:25][C:17]2[N:18]=[C:19]([CH3:24])[CH:20]=[C:15]([NH2:14])[C:16]=2[C:27]=1[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([Br:34])[CH:29]=1

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 68323810HCID 68323810, compound

Product 1

HCID 68323876HCID 68323876, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
200 °C

Procedure

Diphenyl ether (20 mL, 126 mmol) was added to 4-amino-2-bromo-3-(3-bromophenyl)-6-methylthieno[2,3-b]pyridine-5-carboxylic acid (Description 48) (1.861 g, 4.21 mmol). The mixture was heated to 200° C. and stirred at 200° C. for 4 h. The mixture cooled to RT and was stirred overnight at RT. The mixture was then diluted with DCM and purified by chromatography on silica, eluting with a gradient of 0-40% ethyl acetate in cyclohexane, to give the title compound (1.0 g). LCMS (A) m/z: 399 [M+1]+, Rt 0.94 min (acidic).

Workup

  1. temperatureThe mixture cooled to RT
  2. stirringwas stirred overnight at RT
  3. custompurified by chromatography on silica
  4. washeluting with a gradient of 0-40% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-281805953d4345ecbecee6507ed668ca
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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