Diphenyl Ether → 3-Bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine

HRID 573542Notes

Reaction equation

HRID 573542 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]([CH3:16])=[C:14]([Br:15])[C:3]=12.C1(OC2C=CC=CC=2)C=CC=CC=1>>[Br:15][C:14]1[C:3]2[C:2]([NH2:1])=[CH:7][C:6]([CH3:11])=[N:5][C:4]=2[S:12][C:13]=1[CH3:16]

Participants

3

Reactant 2

HCID 7583Diphenyl EtherHCID 683240454-Amino-3-bromo-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylic acid

Product 1

HCID 683238623-Bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amineYield 109.4%

Conditions

Temperature
200 °C

Procedure

To 4-amino-3-bromo-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylic acid (1.95 g, 6.47 mmol) (Description 7) was added diphenyl ether (15 mL, 94 mmol) and the mixture heated at 200° C. for 4 h. This crude mixture was cooled and combined with material (1 g) from a similar reaction. Purification by chromatography on silica gel, eluting with a gradient of 0-50% ethyl acetate in cyclohexane afforded the title compound (1.82 g). LCMS (A) m/z: 257/259 [M+1]+, Rt 0.67 min (acidic).

Workup

  1. customPurification by chromatography on silica gel
  2. washeluting with a gradient of 0-50% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-e87d9b752a294b5e971f5d6f252f6952
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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