Dilithiation of 4-(pivaloylamino)pyridine (5) followed by reaction with tetraisopropylthiuram disulfide(TITD) gave rise to 3-(diisopropyldithiocarbamato)-4-(pivaloylamino)pyridine (6). 3-Mercapto-4H-pyrrolopyridine(2) was synthesized from compound 6 by two methods. The first method was that compound 6 was treated with 5M-HCl to form 2-t-butylthiazolo[5,4-c]pyridine (7) and hydrolysed in refluxing 10％ NaOH and solid NaOH to prepare bis(4-amino-3-pyridyl)disulfide (8). And compound 8 was reacted with 2,5-dimethoxytetrahydrofuran and NaBH$_4$ to afford compound 2. The second method was that compound 6 was hydrolysed with 10％ NaOH and followed to react with 2,5-dimethoxytetrahydrofuran to form compound 11. And then compound 11 was treated with 20％ ethanolic KOH solution to synthesize compound 2.