4-Chloro-1H-pyrrolo[2,3-b]pyridine → N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amine

HRID 1529178Notes

Reaction equation

HRID 1529178 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[NH:8][CH:9]=[CH:10][C:3]=12.[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([NH:24][CH3:25])[CH2:19]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[CH2:11]([N:18]1[CH2:23][CH2:22][CH2:21][CH:20]([N:24]([CH3:25])[C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[NH:8][CH:9]=[CH:10][C:3]=23)[CH2:19]1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

3

Reactant 2

HCID 113894934-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 215125341-Benzyl-N-methylpiperidin-3-amine

Product 1

HCID 59659146N-(1-benzylpiperidin-3-yl)-N-methyl-N-(1H-pyrrolo[2,3-b]pyridin-4-yl)-amineYield 130%

Conditions

Temperature
200 °C

Procedure

A sealed melted mixture of 4-chloro-1H-pyrrolo[2,3-b]pyridine (0.18 g, 0.0012 mol) in 1-benzyl-N-methylpiperidin-3-amine (0.50 g, 0.0024 mol) was heated to 200° C. overnight. The reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL), and the organic phase was washed with sat. NaCl, then dried and was reduced under vacuum to give 500 mg of orange oil. The product was chromatographed with 7% MeOH/DCM, 0.7% NH4OH to give 192 mg of an orange oil (48.8% yield). 1H NMR (400 MHz, CDCl3): δ 7.98 (1H, d); 7.34 (5H, m); 7.08 (1H, d); 6.55 (1H, d); 6.2 (1H, d); 4.15 (1H, t); 3.47 (2H, q); 3.15 (1H); 3.1 (3H, s); 2.9 (1H, d) 2.2-1.6 (6H, m). MS (M+H)+: 322.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate (30 mL) and sat. NaHCO3 (20 mL)
  2. washthe organic phase was washed with sat. NaCl
  3. customdried

Sources & evidence

ORD record
ord-b703f28951534beebd09cf55a79c543f
Source dataset
uspto-grants-2015_07
Patent number
US09090611B2

Reaction notes

Loading…