7-Bromoisoquinoline → HCID 45381506, compound

HRID 2176184Notes

Reaction equation

[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:5]=3[C:4]=2[CH:3]=1)[CH2:13][CH2:12]4.Br[C:19]1[CH:28]=[C:27]2[C:22]([CH:23]=[CH:24][N:25]=[CH:26]2)=[CH:21][CH:20]=1>>[CH:26]1[C:27]2[C:22](=[CH:21][CH:20]=[C:19]([N:7]3[C:8]4[CH:9]=[CH:10][C:2]([CH3:1])=[CH:3][C:4]=4[C:5]4[CH2:15][N:14]5[CH2:13][CH2:12][CH:11]([C:6]3=4)[CH2:17][CH2:16]5)[CH:28]=2)[CH:23]=[CH:24][N:25]=1

Participants

Reactant 2

HCID 122574417-Bromoisoquinoline

HCID 67544841HCID 67544841, compound

Product 1

HCID 45381506HCID 45381506, compound

Procedure

The reaction of 9-methyl-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (226 mg, 1.0 mmol; Example 2B) and 7-bromoisoquinoline (312 mg, 1.5 mmol; Frontier) was performed as described in Example 68 to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.94-2.20 (m, 4H) 2.42 (s, 3H) 2.91-2.98 (m, 1H) 3.08-3.29 (m, 4H) 4.32 (s, 2H) 6.90-6.96 (m, 1H) 6.98-7.04 (m, 1H) 7.22 (s, 1H) 7.73 (dd, J=8, 2 Hz, 1H) 7.94 (d, J=6 Hz, 1H) 8.09 (d, J=2 Hz, 1H) 8.15 (d, J=9 Hz, 1H) 8.53 (d, J=6 Hz, 1H) 9.33 (s, 1H); MS (DCI/NH3) m/z 354 (M+H)+.

Sources & evidence

ORD record: ord-9dc1bff11be34a43af1bd481faa1011d
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09063126B2

Reaction notes

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