Bis(pinacolato)diborane → HCID 67446621, compound

HRID 1853792Notes

Reaction equation

HRID 1853792 reaction equation
Br[C:2]1[CH:12]=[CH:11][C:5]([CH2:6][NH:7][CH:8]([CH3:10])[CH3:9])=[CH:4][CH:3]=1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.Br[C:32]1[C:33]2[C:34]3[CH:47]=[CH:46][S:45][C:35]=3[C:36](=[O:44])[NH:37][C:38]=2[CH:39]=[CH:40][C:41]=1[O:42][CH3:43]>>[CH:8]([NH:7][CH2:6][C:5]1[CH:11]=[CH:12][C:2]([C:32]2[C:33]3[C:34]4[CH:47]=[CH:46][S:45][C:35]=4[C:36](=[O:44])[NH:37][C:38]=3[CH:39]=[CH:40][C:41]=2[O:42][CH3:43])=[CH:3][CH:4]=1)([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 2733548Bis(pinacolato)diboraneHCID 12939866N-[(4-Bromophenyl)methyl]propan-2-amineHCID 674491399-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 67446621HCID 67446621, compoundYield 57%

Procedure

Following General Procedure E, N-(4-bromobenzyl)propan-2-amine (200 mg, 0.88 mmol) was reacted with bis(pinacolato)diboron (240 mg, 0.96 mmol) to afford the crude boronic ester which was reacted with 9-bromo-8-methoxythieno[2,3-c]quinolin-4(5H)-one (270 mg, 0.88 mmol) to afford the desired product (190 mg, 57%) as a light brown solid: 1H NMR (500 MHz, CD3CD2OD) δ 7.68-7.63 (m, 2H), 7.56-7.49 (m, 2H), 7.41-7.34 (m, 3H), 6.04 (dd, J=5.4, 2.4 Hz, 1H), 4.33 (s, 2H), 3.72-3.67 (m, 3H), 3.56-3.50 (m, 1H), 1.45 (dd, J=6.6, 2.2 Hz, 6H).

Workup

  1. customto afford the crude boronic ester which

Sources & evidence

ORD record
ord-c693237329bb42ad993138bc9194ae01
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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