Dimethylformamide → HCID 68630540, compound

HRID 2365247Notes

Reaction equation

HRID 2365247 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]3[CH:29]=[CH:28][CH:27]=[CH:26][C:11]=3[C:12]3[CH2:13][N:14]([C@H:19]4[CH2:24][CH2:23][CH2:22][CH2:21][C@@H:20]4[OH:25])[C:15](=[O:18])[C:16]=3[CH:17]=2)=[CH:4][CH:3]=1.[CH3:30][N:31](C)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>[OH:25][C@H:20]1[CH2:21][CH2:22][CH2:23][CH2:24][C@@H:19]1[N:14]1[CH2:13][C:12]2[C:11]3[CH:26]=[CH:27][CH:28]=[CH:29][C:10]=3[C:9]([CH2:8][C:5]3[CH:4]=[CH:3][C:2]([C:30]#[N:31])=[N:7][CH:6]=3)=[CH:17][C:16]=2[C:15]1=[O:18]

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 86682401HCID 86682401, compound

Product 1

HCID 68630540HCID 68630540, compound

Reagents, catalysts & solvents 2

HCID 11186Zinc cyanide (Zn(CN)2)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

To a solution of 5-[(6-chloropyridin-3-yl)methyl]-2-[(1S,2S)-2-hydroxycyclohexyl]-1,2-dihydro-3H-benzo[e]isoindol-3-one (0.022 g, 0.019 mmol) in 0.5 mL of N,N-dimethylformamide was added zinc cyanide (0.034 g, 0.29 mmol) and tetrakis(triphenylphosphine)palladium (0) (0.039 g, 0.097 mmol). The mixture was irradiated in a microwave reactor at 160° C. for 30 min, cooled to ambient temperature, and purified via preparative reverse phase HPLC and preparative thin layer chromatography, eluting with 50% ethyl acetate in dichloromethane, to provide the title compound that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 398.2 for [M+H]+: 1H NMR (400 MHz, CDCl3) δ 8.62 (s, 1H), 7.92 (d, J=8.1 Hz, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.66 (s, 1H), 7.64-7.58 (m, 2H), 7.51 (d, J=8.1 Hz, 1H), 7.46-7.44 (m, 1H), 4.87-4.71 (m, 2H), 4.45 (s, 2H), 4.21-4.09 (m, 1H), 3.79-3.64 (m, 1H), 2.70-2.67 (m, 1H), 2.24-2.21 (m, 1H), 2.01-1.98 (m, 1H), 1.87-1.83 (m, 1H), 1.72-1.61 (m, 1H), 1.56-1.38 (m, 3H) ppm.

Workup

  1. customThe mixture was irradiated in a microwave reactor at 160° C. for 30 min
  2. custompurified via preparative reverse phase HPLC and preparative thin layer chromatography
  3. washeluting with 50% ethyl acetate in dichloromethane

Sources & evidence

ORD record
ord-7dcd5a555042486c967a535fbfaae171
Source dataset
uspto-grants-2014_04
Patent number
US08697690B2

Reaction notes

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