Acrylonitrile → HCID 54575088, compound

HRID 2190160Notes

Reaction equation

HRID 2190160 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:15]([S:17]([CH3:20])(=[O:19])=[O:18])[CH3:16])=[C:11](I)[CH:12]=2)[O:7][C:6]=1[C:21]1[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=1)=[O:4].[C:28](#[N:31])[CH:29]=[CH2:30].C(N(CC)CC)C>CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:28](/[CH:29]=[CH:30]/[C:11]1[CH:12]=[C:13]2[C:5]([C:3]([NH:2][CH3:1])=[O:4])=[C:6]([C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=3)[O:7][C:8]2=[N:9][C:10]=1[N:15]([CH3:16])[S:17]([CH3:20])(=[O:19])=[O:18])#[N:31]

Participants

6

Reactant 3

HCID 7855AcrylonitrileHCID 8471TriethylamineHCID 545750872-(4-fluorophenyl)-5-iodo-N-methyl-6-(N-methylmethylsulfonamido)furo[2,3-b]pyridine-3-carboxamide

Product 1

HCID 54575088HCID 54575088, compoundYield 70.5%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

2-(4-Fluoro-phenyl)-5-iodo-6-(methanesulfonyl-methyl-amino)-furo[2,3-b]pyridine-3-carboxylic acid methylamide (10 mg, 0.020 mmol), acrylonitrile (1.371 mg, 0.026 mmol), palladium(II) acetate (0.446 mg, 1.987 μmol) and triethylamine (2.77 μl, 0.020 mmol) in DMF (1 ml) were heated under microwave irradiation at 120° C. for 40 min. After LCMS showed predominant conversion to product, the reaction mixture was concentrated to dryness, taken up in DMF, filtered and purified by HPLC to afford the title compound (6 mg, 0.014 mmol, 70.5% yield). MS (ESI) m/z 429.3 (M+1). NMR (400 MHz, CD3CN) δ 8.51 (s, 1H), 8.06-8.03 (m, 2H), 7.94-7.89 (d, 1H, J=17 Hz), 7.34-7.30 (m, 2H), 6.91 (br s, 1H), 6.30-6.26 (d, 1H, J=17 Hz) (s, 1H), 3.31 (s, 3H), 3.12 (s, 3H), 2.91-2.89 (d, 3H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness
  2. filtrationfiltered
  3. custompurified by HPLC

Sources & evidence

ORD record
ord-26d4e45f0bde4ae9a455a51f708f4c03
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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