Methyl 5-((tert-butoxycarbonyl)amino)-4-nitrothiophene-2-carboxylate → Methyl 4-amino-5-(tert-butoxycarbonylamino)thiophene-2-carboxylate

Participants

Reaction Steps

A solution of methyl 5-(tert-butoxycarbonylamino)-4-nitrothiophene-2-carboxylate 88 (0.165 mmol, 50 mg) and palladium on activated carbon (0.083 mmol, 9.79 mg) in methanol (5 mL) was stirred for 1 h at rt with hydrogen gas bubbling through. Additional (0.2 eq) of Pd/C was added and stirred for 1 h. Reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give methyl 4-amino-5-(tert-butoxycarbonylamino)thiophene-2-carboxylate 89 (45 mg, 100%). NMR (400 MHz, CDCl3) 1.52 (s, 9H), 3.83 (s, 3H), 6.85 (br s, 1H), 7.30 (s, 1H). (m/z)=273 (M+H)+.

Provenance & Evidence