2-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amine → tert-butyl 2-(N-(4-bromo-3-methylbenzyl)-2,2-dimethylchroman-6-sulfonamido)acetate

HRID 1805953Notes

Reaction equation

HRID 1805953 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][C:45]=1[CH3:52]>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][C:45]=1[CH3:52]

Participants

5

Reactant 3

HCID 35138512-((1,1-Dimethylethyl)imino)-N,N-diethylhexahydro-1,3-dimethyl-2lambda5-1,3,2-diazaphosphorin-2-amineHCID 118322651-Bromo-4-(bromomethyl)-2-methylbenzeneHCID 58409094Tert-butyl 2-(2,2-dimethylchroman-6-sulfonamido)acetate

Product 1

HCID 58409101tert-butyl 2-(N-(4-bromo-3-methylbenzyl)-2,2-dimethylchroman-6-sulfonamido)acetateYield 68.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
90 °C

Procedure

To the 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)-2-methylbenzene (631 mg, 2.391 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 (516 mg, 68% yield). 1H NMR (500 MHz, CDCl3) δ 7.58 (d, J=2.2 Hz, 1H), 7.57 (s, 1H), 7.44 (d, J=8.1 Hz, 1H), 7.09 (s, 1H), 6.92 (dd, J=8.2, 2.1 Hz, 1H), 6.84 (d, J=9.3 Hz, 1H), 4.42 (s, 2H), 3.78 (s, 2H), 2.79 (t, J=6.8 Hz, 2H), 2.34 (s, 3H), 1.82 (t, J=6.7 Hz, 2HLRMS [ESI, MH+] m/z calcd for C25H33BrNO5S 538.13, found 538.1.

Workup

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

Sources & evidence

ORD record
ord-ecf99c8e8f6c4e04bfe22b6087ff7e87
Source dataset
uspto-grants-2013_01
Patent number
US08354548B2

Reaction notes

Loading…