Dimethylacetamide → HCID 59326517, compound

HRID 238637Notes

Reaction equation

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

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of [6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (29 mg, 0.07 mmol, methyl ester of example 12-1), zinc cyanide (10 mg, 0.084 mmol), tetrakis(triphenylphosphine)palladium(0) (18 mg, 0.014 mmol) and N,N-dimethylacetamide (0.2 mL) was stirred at 150° C. for 24 hours under an argon atmosphere. The reaction mixture was diluted with water (5 mL), and extracted with ethyl acetate (20 mL×2). The combined organic layers were washed with brine (20 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by preparative TLC (30% ethyl acetate in petroleum ether) to give [6-cyano-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-acetic acid methyl ester (17 mg) as a white solid.

Workup

extractionextracted with ethyl acetate (20 mL×2)
washThe combined organic layers were washed with brine (20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customThe residue was purified by preparative TLC (30% ethyl acetate in petroleum ether)

Sources & evidence

ORD record: ord-3b7a3bd459db4d54a97567b22902ce1b
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08642629B2

Reaction notes

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