Sodium Hydroxide → 4-Amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylic acid

HRID 573580Notes

Reaction equation

[NH2:1][C:2]1[C:7]([C:8]([O:10]CC)=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:18])=[C:16]([CH3:17])[C:3]=12.[OH-].[Na+]>C(O)C>[NH2:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([CH3:13])[N:5]=[C:4]2[S:14][C:15]([Br:18])=[C:16]([CH3:17])[C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 4-amino-2-bromo-3,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (Description 31) (857 mg, 2.60 mmol) in ethanol (25 mL) was added aqueous NaOH (2M) (2.60 mL, 5.21 mmol) and reaction mixture stirred at 100° C. for 4 h. The mixture was then cooled to RT before the solvent was removed in vacuo. The residue was then taken-up in water (20 mL) before acidifying with aqueous HCl (2M) (2 mL) to form a precipitate. The mixture was then subjected to a centrifuge and the aqueous solution was then decanted off and the solid residue dried under vacuum, to afford the title compound (720 mg). LCMS (A) m/z: 301/303 [M+1]+, Rt 0.67 min (acidic).

Workup

temperatureThe mixture was then cooled to RT before the solvent
customwas removed in vacuo
customto form a precipitate
customthe aqueous solution was then decanted off
customthe solid residue dried under vacuum

Sources & evidence

ORD record: ord-dccae0adc4b04abea0f43bdc92c1761a
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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