Bis(pinacolato)diborane → HCID 67448658, compound

HRID 1853789Notes

Reaction equation

HRID 1853789 reaction equation
Br[C:2]1[CH:13]=[CH:12][C:5]([CH2:6][N:7]([CH2:10][CH3:11])[CH2:8][CH3:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:33]1[C:34]2[C:35]3[CH:48]=[CH:47][S:46][C:36]=3[C:37](=[O:45])[NH:38][C:39]=2[CH:40]=[CH:41][C:42]=1[O:43][CH3:44]>>[CH2:8]([N:7]([CH2:6][C:5]1[CH:12]=[CH:13][C:2]([C:33]2[C:34]3[C:35]4[CH:48]=[CH:47][S:46][C:36]=4[C:37](=[O:45])[NH:38][C:39]=3[CH:40]=[CH:41][C:42]=2[O:43][CH3:44])=[CH:3][CH:4]=1)[CH2:10][CH3:11])[CH3:9]

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 10999178(p-bromobenzyl)diethyl amineHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67448658HCID 67448658, compoundYield 25%

Procedure

Following General Procedure E, N-(4-bromobenzyl)-N-ethylethanamine (200 mg, 0.83 mmol) was reacted with bis(pinacolato)diboron (230 mg, 0.91 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (260 mg, 0.83 mmol) to afford the desired product (58 mg, 25%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.69 (d, J=8.2 Hz, 2H), 7.60-7.54 (m, 2H), 7.46-7.43 (m, 2H), 7.41 (d, J=9.1 Hz, 1H), 5.99 (d, J=5.4 Hz, 1H), 4.50 (s, 2H), 3.75 (s, 3H), 3.41-3.32 (m, 4H), 1.44 (t, J=7.3 Hz, 6H).

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-d67d0ce446904769b47991b1c3460b7f
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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