Dimethylformamide → HCID 68550962, compound

3-Ethyl-1H-pyrrolo[2,3-b]pyridine (0.91 g, 6.2 mmol) and KOtBu (1.39 g, 12.4 mmol) are dissolved in DMF (28 mL) and stirred for 2 h at rt. While vigorously sparging with nitrogen, NH2Cl (92 ml 0.15 M in ether) is added in portions. The reaction mixture is stirred at rt for 2 h. The mixture is cooled 0° C. and then quenched with Na2S2O3 (2.7 g) in water (50 mL). After standing at rt for 18 h, the mixture is concentrated, triturated in DCM and filtered. The filtrate is concentrated and chromatographed through silica gel eluting with 10% MeOH in DCM to afford 3-ethyl-pyrrolo[2,3-b]pyridin-1-yl-amine (380 mg). MS: 162 (M+H); 1H NMR (300 MHz, CDCl3): δ 8.32 (d, 1H), 7.90 (d, 1H), 7.04-7.13(m, 2H), 4.96 (broad s, 2H), 2.76 (q, 2H), 1.33 (t, 3H).

1. customWhile vigorously sparging with nitrogen, NH2Cl (92 ml 0.15 M in ether)
2. additionis added in portions
3. stirringThe reaction mixture is stirred at rt for 2 h
4. temperatureThe mixture is cooled 0° C.
5. customquenched with Na2S2O3 (2.7 g) in water (50 mL)
6. waitAfter standing at rt for 18 h
7. concentrationthe mixture is concentrated
8. customtriturated in DCM
9. filtrationfiltered
10. concentrationThe filtrate is concentrated
11. customchromatographed through silica gel eluting with 10% MeOH in DCM

ORD record

ord-e2a6cb5074474789b935c82a1db71162

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08258130B2