تفاعل #2469287

معادلة التفاعل

3-methyl-1H-pyrrolo[3,2-c]pyridine

KOtBu

DMF

BOC2O

→

3-methyl-pyrrolo [3,2-c]pyridin-1-yl amine

المردود 35.0%

ظروف التفاعل

المعالجة

1. 1
   أخرىis purged with N2
2. 2
   workup.ADDITIONChloramine in ether (0.15 M, 145 mL) is added
3. 3
   workup.STIRRINGthe mixture is stirred for 20 min
4. 4
   درجة الحرارةThe reaction is cooled to 00 C
5. 5
   workup.ADDITIONand a solution of Na2S2O3 (800 mg) in water (130 mL) is added
6. 6
   workup.STIRRINGThe mixture is stirred for 10 min at 00 C
7. 7
   تركيز, and then concentrated in vacuo
8. 8
   أخرىThe residue is triturated in DCM
9. 9
   ترشيحfiltered
10. 10
    workup.ADDITIONDCM is added to the filtrate
11. 11
    درجة الحرارةcooled to 0° C.
12. 12
    تركيزThe mixture is concentrated in vacuo
13. 13
    أخرىthe residue is purified by silica gel chromatography
14. 14
    غسيلeluting with 10% MeOH in DCM

الإجراء التجريبي

A mixture of 3-methyl-1H-pyrrolo[3,2-c]pyridine (1.91 g, 14.47 mmol) and KOtBu (3.25 g, 28.9 mmol) in DMF (65 mL) is purged with N2 and stirred at rt for 2 h. Chloramine in ether (0.15 M, 145 mL) is added and the mixture is stirred for 20 min. The reaction is cooled to 00 C. and a solution of Na2S2O3 (800 mg) in water (130 mL) is added. The mixture is stirred for 10 min at 00 C., and then concentrated in vacuo. The residue is triturated in DCM and filtered. DCM is added to the filtrate, cooled to 0° C. and treated with BOC2O (793 mg, 3.6 mmol). The mixture is concentrated in vacuo, and the residue is purified by silica gel chromatography eluting with 10% MeOH in DCM to afford 3-methyl-pyrrolo [3,2-c]pyridin-1-yl amine (842 mg, 35%). MS: 148 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.85 (s, 1H), 8.36 (d, 1H), 7.32 (d, 1H), 6.95 (s, 1H) 4.77 (s, 2H), 2.37 (s, 3H).

المصدر