7-Bromoquinoline → HCID 45381278, compound

HRID 2176201Notes

Reaction equation

HRID 2176201 reaction equation
[CH2:1]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[NH:7][C:6]=2[CH:5]2[CH2:15][CH2:16][N:2]1[CH2:3][CH2:4]2.Br[C:18]1[CH:27]=[C:26]2[C:21]([CH:22]=[CH:23][CH:24]=[N:25]2)=[CH:20][CH:19]=1>>[N:25]1[C:26]2[C:21](=[CH:20][CH:19]=[C:18]([N:7]3[C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=4[C:14]4[CH2:1][N:2]5[CH2:3][CH2:4][CH:5]([C:6]3=4)[CH2:15][CH2:16]5)[CH:27]=2)[CH:22]=[CH:23][CH:24]=1

Participants

3

Reactant 2

HCID 5212597-BromoquinolineHCID 67545626HCID 67545626, compound

Product 1

HCID 45381278HCID 45381278, compound

Procedure

The reaction of 3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (212 mg, 1.0 mmol; Example 187A) and 7-bromoquinoline (312 mg, 1.5 mmol; Ark Pharm) was performed as described in Example 68 to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.96-2.23 (m, 4H) 2.99-3.05 (m, 1H) 3.10-3.30 (m, 4H) 4.37 (s, 2H) 7.07-7.21 (m, 3H) 7.40-7.49 (m, 1H) 7.59-7.69 (m, 2H) 7.97 (d, J=2 Hz, 1H) 8.17 (d, J=9 Hz, 1H) 8.50 (d, J=7 Hz, 1H) 8.95 (dd, J=4, 2 Hz, 1H); MS (DCI/NH3) m/z 340 (M+H)+.

Sources & evidence

ORD record
ord-6c6b55a067394ac1838e0be9252faeba
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

Loading…