Triethylamine → HCID 59463785, compound

HRID 1713350Notes

Reaction equation

[F:1][C:2]([F:25])([F:24])[C:3]([CH2:8][C:9]1([CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:17]=2)[O:12][CH2:11][CH2:10]1)([OH:7])[CH2:4][C:5]#[CH:6].[C:26]([C:28]1[CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[C:31](OS(C(F)(F)F)(=O)=O)=[C:30]([CH3:45])[CH:29]=1)#[N:27].C(N(CC)CC)C>C1COCC1.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:45][C:30]1[CH:29]=[C:28]([CH:33]=[C:32]([N+:34]([O-:36])=[O:35])[C:31]=1[C:6]#[C:5][CH2:4][C:3]([OH:7])([CH2:8][C:9]1([CH3:23])[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([S:19]([CH3:22])(=[O:21])=[O:20])[CH:17]=2)[O:12][CH2:11][CH2:10]1)[C:2]([F:1])([F:24])[F:25])[C:26]#[N:27]

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of 330 mg (0.88 mmol) of 1,1,1-trifluoro-2-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-4-yn-2-ol, 270 mg (0.88 mmol) of trifluoromethanesulfonic acid 4-cyano-2-methyl-6-nitrophenyl ester, 310 mg (0.04 mmol) of bis(triphenylphosphine)palladium (II) dichloride, 17 mg (0.09 mmol) of copper (I) iodide, and 0.25 mL of anhydrous triethylamine in 2 mL of THF was warmed at 60° C. in a sealed tube in the microwave. After 20 minutes, the mixture was adsorbed onto CELITE® filter aid and chromatographed on silica gel eluting with ethyl acetate-hexanes (gradient: 0-30% EtOAc) to afford 205 mg (44%) of 3-methyl-5-nitro-4-[5,5,5-trifluoro-4-hydroxy-4-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-1-ynyl]benzonitrile as a brown oil.

Workup

filtrationfilter aid
customchromatographed on silica gel eluting with ethyl acetate-hexanes (gradient: 0-30% EtOAc)

Sources & evidence

ORD record: ord-c7884d4c7a2f4b9c88850447e6ad4b97
Source dataset: uspto-grants-2010_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07795272B2

Reaction notes

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