Dimethylformamide → HCID 45123327, compound

HRID 452630Notes

Reaction equation

[C:1]([N:4]1[C:8]2=[N:9][CH:10]=[CH:11][C:12](I)=[C:7]2[CH:6]=[C:5]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:3])[CH3:2].[CH3:22][N:23](C)C=O>C(OCC)(=O)C.[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>[C:1]([N:4]1[C:8]2[N:9]=[CH:10][CH:11]=[C:12]([C:22]#[N:23])[C:7]=2[CH:6]=[C:5]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-acetyl-4-iodo-2-(2-phenylethyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.56 mmol), zinc cyanide (246 mg, 1.41 mmol), tetrakis(triphenylphosphine)palladium(0) (148 mg, 0.128 mmol) and N,N-dimethylformamide (20 mL) was stirred under an argon atmosphere at 80° C. for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1), and crystallized from hexane to give the title compound (472 mg, yield 64%) as colorless crystals.

Workup

washwashed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-0/1)
customcrystallized from hexane

Sources & evidence

ORD record: ord-c5b321a5e8a245c4a31aa41de927c6c8
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08492378B2

Reaction notes

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