Hydrochloric Acid → HCID 67125611, compound

HRID 1184926Notes

Reaction equation

HRID 1184926 reaction equation
[C:1]([C:3]([C:6]1[CH:7]=[C:8]([CH:20]=[CH:21][CH:22]=1)[C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[C:14](I)[CH:13]=1)=[O:10])([CH3:5])[CH3:4])#[N:2].[CH2:23]([O:25]C([Sn](CCCC)(CCCC)CCCC)=C)[CH3:24].Cl>C1(C)C=CC=CC=1.O1CCOCC1.C(OCC)(=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:23]([C:14]1[CH:13]=[C:12]([NH:11][C:9](=[O:10])[C:8]2[CH:20]=[CH:21][CH:22]=[C:6]([C:3]([C:1]#[N:2])([CH3:5])[CH3:4])[CH:7]=2)[CH:17]=[CH:16][C:15]=1[CH3:18])(=[O:25])[CH3:24]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 619414Stannane, tributyl(1-ethoxyethenyl)-HCID 67125657HCID 67125657, compound

Product 1

HCID 67125611HCID 67125611, compoundYield 73.5%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of 3-(2-cyanopropan-2-yl)-N-(3-iodo-4-methylphenyl)benzamide 111 (1.546 mmol, 625 mg), 1-ethoxyvinyltri-n-butyltin (4.64 mmol, 1.567 mL) and bis(triphenylphosphine)palladium(II) chloride (0.155 mmol, 109 mg) in toluene (5 mL) was stirred at 100° C. for 2 h. Cooled down to room temperature, 4N HCl in dioxane (1 mL) was added and stirred for 1 h. Diluted with ethyl acetate, filtrated and evaporated. Purification by chromatography (0-5% ethyl acetate in CH2Cl2) gave N-(3-acetyl-4-methylphenyl)-3-(2-cyanopropan-2-yl)benzamide 112 (364 mg, 73.5%). NMR (400 MHz, CDCl3) 1.79 (s, 6H), 2.52 (s, 3H), 2.62 (s, 3H), 7.26 (d, J=8.2 Hz, 1H), 7.55 (m, 2H), 7.72 (d, J=7.8 Hz, 1H), 7.81 (d, J=7.4 Hz, 1H), 7.91 (br s, 1H), 8.00 (t, J=1.9 Hz, 1H), 8.15 (d, J=2.3 Hz, 1H).

Workup

  1. filtrationfiltrated
  2. customevaporated
  3. customPurification by chromatography (0-5% ethyl acetate in CH2Cl2)

Sources & evidence

ORD record
ord-c028c67b36eb4c2dbb106286c1ab4721
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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