Diphenyl Ether → HCID 68323880, compound

HRID 573581Notes

Reaction equation

HRID 573581 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:16])=[C:14]([CH3:15])[C:3]=12.C1(OC2C=CC=CC=2)C=CC=CC=1>CO>[Br:16][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[CH3:15]

Participants

4

Reactant 2

HCID 7583Diphenyl EtherHCID 683237964-Amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 68323880HCID 68323880, compoundYield 56.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylic acid (Description 61) (720 mg, 2.391 mmol) and diphenyl ether (3.80 mL, 23.91 mmol) was heated to 200° C. for 48 h. The mixture was then cooled to RT, taken-up in MeOH (10 mL) and purified on silica, eluting with a gradient of 0-20% 2M NH3 in MeOH in DCM. Further purification by SCX, eluting with 0-100% 2M NH3 in MeOH in MeOH afforded the title compound (350 mg). LCMS (A) m/z: 257/259 [M+1]+, Rt 1.10 min (basic).

Workup

  1. custompurified on silica
  2. washeluting with a gradient of 0-20% 2M NH3 in MeOH in DCM
  3. customFurther purification by SCX
  4. washeluting with 0-100% 2M NH3 in MeOH in MeOH

Sources & evidence

ORD record
ord-25fd4de62105405f91918a7591a99e0f
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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