6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinoline → HCID 53251425, compound

HRID 37802Notes

Reaction equation

HRID 37802 reaction equation
Br[C:2]1[C:10]2[NH:9][C:8]3[CH:11]4[CH2:17][CH2:16][N:14]([CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1)[CH2:13][CH2:12]4.[N:18]1[C:27]2[C:22](=[CH:23][C:24](B3OC(C)(C)C(C)(C)O3)=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1>>[N:18]1[C:27]2[C:22](=[CH:23][C:24]([C:2]3[C:10]4[NH:9][C:8]5[CH:11]6[CH2:17][CH2:16][N:14]([CH2:15][C:7]=5[C:6]=4[CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]6)=[CH:25][CH:26]=2)[CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 162177846-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)quinolineHCID 672401637-bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

Product 1

HCID 53251425HCID 53251425, compound

Procedure

7-Bromo-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole (146 mg, 0.5 mmol, Example 1B) was coupled with 6-quinolineboronic acid pinacol ester (191 mg, 0.75 mmol, Aldrich) following the procedure described in Example 4. Purification by preparative reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 40-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] gave the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 1.99-2.18 (m, 4 H) 3.02-3.30 (m, 5 H) 4.29 (s, 2 H) 7.10-7.24 (m, 2 H) 7.36 (d, J=8 Hz, 1 H) 7.58 (dd, J=8, 4 Hz, 1 H) 8.04-8.10 (m, 1 H) 8.13-8.22 (m, 2 H) 8.45 (d, J=8 Hz, 1 H) 8.86 (dd, J=4, 2 Hz, 1 H); MS (DCI/NH3) m/z 340 (M+H)+.

Workup

  1. customPurification by preparative reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 40-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

Sources & evidence

ORD record
ord-38c701269cb746cf8776851c270e196f
Source dataset
uspto-grants-2013_09
Patent number
US08524703B2

Reaction notes

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