Potassium Iodide → HCID 11639149, compound

HRID 1158702Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([NH:9][C:10](=[O:19])[CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)=[C:4]([Cl:20])[CH:3]=1.Cl[CH2:22][CH2:23][O:24][CH2:25][CH2:26]Cl.[I-].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O>[Cl:20][C:4]1[CH:3]=[C:2]([N:1]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)[CH:7]=[C:6]([CH3:8])[C:5]=1[NH:9][C:10](=[O:19])[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=1

Participants

Conditions

Temperature: 180 °C

Procedure

N-(4-Amino-2-chloro-6-methyl-phenyl)-2-(3-fluoro-phenyl)-acetamide (616 mg), bis-(2-chloroethyl)ether (260 μL) and potassium iodide (400 mg) were mixed in dry N,N-dimethylformamide (11 mL) and heated to 180° C. for 30 minutes in a sealed microwave process vial. 5% aqueous sodium bicarbonate (100 mL) was added and the mixture was extracted with ethyl acetate (3×80 mL). The combined organic phases were washed with water (2×100 mL), brine (1×100 mL), dried over sodium sulfate and concentrated in vacuo. The crude product was purified by flash chromatography to furnish 236 mg (31%) of the title compound as a white solid. LC-MS (m/z) 363 (MH+); tR=2.56, (UV, ELSD) 96%, 99%. NMR (500 MHz, DMSO-d6): 2.04 (s, 3H), 3.10 (m, 4H), 3.65 (s, 2H), 3.70 (m, 4H), 6.79 (d, 1H), 6.85 (d, 1H), 7.07 (dt, 1H), 7.19 (m, 2H), 7.37 (m, 1H), 9.52 (s, 1H).

Workup

extractionthe mixture was extracted with ethyl acetate (3×80 mL)
washThe combined organic phases were washed with water (2×100 mL), brine (1×100 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-1e0a6824d561408f87c64b4213a658ea
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07812023B2

Reaction notes

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