Ammonium Hydroxide → 3-Bromothieno[3,2-c]pyridin-4-amine

HRID 17138Notes

Reaction equation

HRID 17138 reaction equation
[Br:1][C:2]1[C:6]2[C:7](Cl)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1.[NH4+:12].[OH-]>O1CCOCC1>[Br:1][C:2]1[C:6]2[C:7]([NH2:12])=[N:8][CH:9]=[CH:10][C:5]=2[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 184507733-Bromo-4-chlorothieno(3,2-c)pyridine

Product 1

HCID 184507973-Bromothieno[3,2-c]pyridin-4-amineYield 94%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 3-bromo-4-chlorothieno[3,2-c]pyridine (prepared according to the procedure described in Bull. Soc. Chim. Belges 1970, 79, 407-414, 3 g, 12 mmol), concentrated aqueous NH4OH (100 mL), and p-dioxane (100 mL) was sealed in a stainless steel, high-pressure reactor and stirred for 18 hours at 150° C. The mixture was concentrated to half its original volume, diluted with water, and extracted with ethyl acetate. The combined organic extracts were washed with brine, dried (MgSO4), filtered, and concentrated to provide 2.6 g (94%) of the desired product. 1H NMR (DMSO-d6, 400MHz) δ 7.83 (d, 1H), 7.77 (s, 1H), 7.26 (d, 1H), 6.48 (br s, 2H); MS m/e 229 (M+H)+.

Workup

  1. customprepared
  2. concentrationThe mixture was concentrated to half its original volume
  3. additiondiluted with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-e881c0334a2a48b98860a4e212b56dcb
Source dataset
uspto-grants-2010_06
Patent number
US07737160B2

Reaction notes

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