Ammonium Hydroxide → HCID 66760533, compound

HRID 389542Notes

Reaction equation

HRID 389542 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[C:6](Cl)[N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1.[OH-].[NH4+:13]>O1CCOCC1>[Br:1][C:2]1[C:10]2[C:5](=[C:6]([NH2:13])[N:7]=[CH:8][CH:9]=2)[S:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 72207405HCID 72207405, compound

Product 1

HCID 66760533HCID 66760533, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

To a solution of 3-bromo-7-chlorothieno[2,3-c]pyridine (200 mg, 0.805 mmol) in 1,4-dioxane (2.6 mL) was added 28% ammonium hydroxide (2.2 mL, 22 mmol). The mixture was heated in a microwave at 140° C. for 6 h and then concentrated. The residue was suspended in water (15 mL) and extracted with 5% methanol:dichloromethane (5×10 mL). The combined organic fractions were dried over sodium sulfate, filtered, and concentrated. Purification by ISCO chromatography (0 to 5% methanol:dichloromethane) afforded 27 mg (15%) of the title compound as a light yellow solid. 1H NMR (400 MHz, CDCl3): δ 8.10 (d, J=5.8 Hz, 1 H), 7.58 (s, 1 H), 7.18 (d, J=5.6 Hz, 1 H), 4.87 (br. s., 2 H); MS (ESI): 229.04, 231.00 [M+H]+; HPLC tR=2.19 min (ZQ3, polar—4 min).

Workup

  1. concentrationconcentrated
  2. extractionextracted with 5% methanol
  3. dry with materialThe combined organic fractions were dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customPurification by ISCO chromatography (0 to 5% methanol:dichloromethane)

Sources & evidence

ORD record
ord-4b5db475022848cab827391f41ba3a4d
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

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