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

HRID 573541Notes

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]([CH3:18])=[C:16]([Br:17])[C:3]=12.[OH-].[Na+].Cl>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]([CH3:18])=[C:16]([Br:17])[C:3]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of ethyl 4-amino-3-bromo-2,6-dimethylthieno[2,3-b]pyridine-5-carboxylate (5 g, 15.19 mmol) (Description 6) in ethanol (50 mL) was added aqueous NaOH (3M) (20.25 mL, 60.8 mmol) and the mixture stirred at 100° C. for 1 h. The reaction mixture was cooled and combined with material (4.43 g) from a similar reaction. The combined solution was acidified with aqueous HCl (1M) to pH 6-7. Ethanol was removed in vacuo. Water (50 mL) was added and the mixture extracted with DCM (5×50 mL). The combined organics were dried over MgSO4, filtered and solvent removed in vacuo, to afford the title compound (2.98 g). LCMS (A) m/z: 301/303 [M+1]+, Rt 0.73 min (acidic).

Workup

temperatureThe reaction mixture was cooled
customEthanol was removed in vacuo
additionWater (50 mL) was added
extractionthe mixture extracted with DCM (5×50 mL)
dry with materialThe combined organics were dried over MgSO4
filtrationfiltered
customsolvent removed in vacuo

Sources & evidence

ORD record: ord-f7f83ef3d8c14ae0a3a12ebac80611d4
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09029545B2

Reaction notes

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