Ethanol → N-isobutyl-2-methyl-2-(3'-nitrobiphenyl-4-yl)propanamide

HRID 1175571Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([CH3:17])([CH3:16])[C:9]([NH:11][CH2:12][CH:13]([CH3:15])[CH3:14])=[O:10])=[CH:4][CH:3]=1.CCO.C([O-])([O-])=O.[Na+].[Na+].[N+:27]([C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][CH:35]=1)([O-:29])=[O:28]>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[CH2:12]([NH:11][C:9](=[O:10])[C:8]([CH3:17])([C:5]1[CH:6]=[CH:7][C:2]([C:34]2[CH:33]=[CH:32][CH:31]=[C:30]([N+:27]([O-:29])=[O:28])[CH:35]=2)=[CH:3][CH:4]=1)[CH3:16])[CH:13]([CH3:15])[CH3:14]

Participants

Conditions

Temperature: 150 °C

Procedure

2-(4-Bromophenyl)-N-isobutyl-2-methylpropanamide (Example 1a) (100 mg, 0.33 mmol) was weigh out in a microwave vial and dissolved in 3 ml of DME, 2 ml of EtOH and 1.5 ml of water followed by addition of Na2CO3 (70 mg, 0.66 mmol) and 3-nitrophenylboronic acid (67 mg, 0.4 mmol). Pd(PPh3)4 (8 mg, 6.6 μmol) was then added and the tube was immediately sealed. The reaction mixture was heated in a Smith Synthesizer at 150° C. for 5 min. The solution was filtered and the compound purified by preparative HPLC to yield 75 mg (67%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.8 (d, 6H), 1.65 (s, 6H), 1.67-1.70 (m,1H), 3 (dd, 2H), 5.2 (broad, 1H), 7.5(d, 2H), 7.6 (d, 3H), 7.9 (d, 1H), 8.2 (dd, 1H), 8.4 (d, 1H). MS (M+H, 341).

Workup

customthe tube was immediately sealed
filtrationThe solution was filtered
customthe compound purified by preparative HPLC

Sources & evidence

ORD record: ord-60a5c9845957427b98636298d80a7b19
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842324B2

Reaction notes

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