1,2,3,4-Tetrahydroquinoline → HCID 59612418, compound

HRID 1889999Notes

Reaction equation

HRID 1889999 reaction equation
Br[C:2]1[C:3]2[N:4]([N:8]=[C:9](Cl)[N:10]=2)[CH:5]=[CH:6][CH:7]=1.[NH:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH2:15][CH2:14][CH2:13]1>>[N:10]1[C:9]([N:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15][CH2:14][CH2:13]2)=[N:8][N:4]2[C:5]([N:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH2:15][CH2:14][CH2:13]3)=[CH:6][CH:7]=[CH:2][C:3]=12

Participants

3

Reactant 2

HCID 694601,2,3,4-TetrahydroquinolineHCID 674813708-Bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine

Product 1

HCID 59612418HCID 59612418, compound

Procedure

1,1′-[1,2,4]triazolo[1,5-a]pyridine-2,5-diyldi-1,2,3,4-tetrahydroquinoline was prepared from 8-bromo-2-chloro-[1,2,4]triazolo[1,5-a]pyridine (500.0 mg, 2.15 mmol) and 1,2,3,4-tetrahydro-quinoline (274.0 mg, 2.04 mmol) in a manner analogous to Example 2d. Byproduct was isolated as a brown solid (0.033 g, 4%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.14 (d, J=8.2 Hz, 1H), 7.40-7.35 (m, 1H), 7.32-7.28 (m, 1H), 7.15-7.05 (m, 3H), 6.98 (t, J=7.5 Hz, 1H), 6.91-6.84 (m, 2H), 6.69-6.62 (m, 2H), 4.09-4.05 (m, 2H), 3.88-3.83 (m, 2H), 2.93 (t, J=6.4 Hz, 2H), 2.82 (t, J=6.4 Hz, 2H), 2.10-1.80 (m, 4H). MS=382 (MH)+.

Sources & evidence

ORD record
ord-893d5a084163444d8624d6f87d3908f3
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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