Aniline → N-ethyl-N-isopropylpropan-2-amine 2-(4-(methoxycarbonyl)phenyl)-2-(phenylamino)acetate

HRID 1255051Notes

Reaction equation

Br[CH:2]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=1)[C:3]([OH:5])=[O:4].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[CH3:23][CH2:24][N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27]>C(#N)C>[CH3:15][O:14][C:12]([C:9]1[CH:10]=[CH:11][C:6]([CH:2]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:3]([OH:5])=[O:4])=[CH:7][CH:8]=1)=[O:13].[CH2:24]([N:25]([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])[CH3:23]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Bromo-2-(4-(methoxycarbonyl)phenyl)acetic acid (700 mg, 2.56 mmol), aniline (0.23 mL, 2.56 mmol), and DIPEA (0.94 mL, 5.38 mmol) are dissolved in acetonitrile (5 mL). The reaction is stirred at 100° C. under microwave irradiation for 15 minutes. Acetonitrile is evaporated and the residue is dissolved in DCM and washed with water and brine. The organic layer is dried (Na2SO4), filtered and evaporated. The crude compound is purified by flash chromatography (DCM/MeOH=9/1) to obtain intermediate I142 as a white solid (381 mg, 37% yield).

Workup

customAcetonitrile is evaporated
dissolutionthe residue is dissolved in DCM
washwashed with water and brine
dry with materialThe organic layer is dried (Na2SO4)
filtrationfiltered
customevaporated
customThe crude compound is purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record: ord-83a3399676454637bc46af66c33cb0bb
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08455646B2

Reaction notes

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