Benzenemethanamine, 4-bromo-N-methyl- → HCID 67447322, compound

HRID 1853790Notes

Reaction equation

HRID 1853790 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH3:10])=[CH:4][CH:3]=1.Br[C:12]1[C:13]2[C:14]3[CH:27]=[CH:26][S:25][C:15]=3[C:16](=[O:24])[NH:17][C:18]=2[CH:19]=[CH:20][C:21]=1[O:22][CH3:23]>>[CH3:23][O:22][C:21]1[CH:20]=[CH:19][C:18]2[NH:17][C:16](=[O:24])[C:15]3[S:25][CH:26]=[CH:27][C:14]=3[C:13]=2[C:12]=1[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH3:10])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 485400Benzenemethanamine, 4-bromo-N-methyl-HCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67447322HCID 67447322, compoundYield 42%

Procedure

Following General Procedure E, 1-(4-bromophenyl)-N-methylmethanamine (200 mg, 1.0 mmol) was reacted to bis(pinacoato)diboron (280 mg, 1.1 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (310 mg, 1.0 mmol) to afford the desired product (145 mg, 42%) as a white solid: 1H NMR (500 MHz, CD3OD) δ 7.65 (d, J=8.1 Hz, 2H), 7.58-7.52 (m, 2H), 7.42-7.35 (m, 3H), 6.02 (d, J=5.4 Hz, 1H), 4.33 (s, 2H), 3.73 (s, 3H), 2.83 (s, 3H).

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-9e5ffceaf92d4497b9b001eea50f5634
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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