4-Bromobenzyl bromide → tert-butyl 2-(N-(4-bromobenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

HRID 1805950Notes

Reaction equation

[CH3:1][C:2]1([CH3:24])[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([S:12]([NH:15][CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])(=[O:14])=[O:13])[CH:8]=2)[O:3]1.CCN(P1(N(C)CCCN1C)=NC(C)(C)C)CC.[Br:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50]Br)=[CH:46][CH:45]=1>CC#N>[Br:43][C:44]1[CH:49]=[CH:48][C:47]([CH2:50][N:15]([CH2:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[S:12]([C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[O:3][C:2]([CH3:24])([CH3:1])[CH2:11][CH2:10]3)(=[O:14])=[O:13])=[CH:46][CH:45]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate (500 mg, 1.407 mmol) in MeCN (15 mL) was added resin-supported BEMP (786 mg, 1.547 mmol) and 1-bromo-4-(bromomethyl)benzene (602 mg, 2.409 mmol). The mixture was heated in a microwave synthesizer at 90° C. for 3 hours. The reaction mixture was filtered, rinsed alternatively by dichloromethane and methanol. The filtrate was concentrated to give a reddish orange residue, which was purified by silica chromatography to obtain a white powder (632 mg, 86% yield). 1H NMR (500 MHz, CDCl3) δ 7.59-7.55 (m, 2H), 7.43 (d, J=8.3 Hz, 2H), 7.14 (d, J=8.3 Hz, 2H), 6.84 (d, J=9.1 Hz, 1H), 4.45 (s, 2H), 3.78 (s, 2H), 2.79 (t, J=6.7 Hz, 2H), 1.83 (t, J=6.7 Hz, 2H), 1.35 (s, 6H), 1.33 (s, 9H). LRMS [ESI, MH+] m/z calcd for C24H31BrNO5S 524.11, found 524.1.

Workup

filtrationThe reaction mixture was filtered
washrinsed alternatively by dichloromethane and methanol
concentrationThe filtrate was concentrated
customto give a reddish orange residue, which
customwas purified by silica chromatography

Sources & evidence

ORD record: ord-9b09b3c1c49c4e49b6c0cb24455b7aae
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08354548B2

Reaction notes

Loading…