Triethylamine → HCID 67003656, compound

HRID 2362658Notes

Reaction equation

[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9](I)[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1.C(N(CC)CC)C.[C]=O>CO.C(#N)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[Cl:1][C:2]1[C:3]([C:22]2[S:26][C:25]([C:27]3([O:31][CH2:32][O:33][CH3:34])[CH2:30][CH2:29][CH2:28]3)=[N:24][CH:23]=2)=[C:4]2[CH:10]=[C:9]([C:32]([O:31][CH3:27])=[O:33])[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]2=[N:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a 50 ml pressure bottle, a solution of Example 1F (0.15 g, 0.238 mmol) and triethylamine (0.066 ml, 0.476 mmol) in methanol (2 ml) and acetonitrile (2 mL) was treated with [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.017 g, 0.024 mmol). The mixture was pressurized with carbon monoxide (60 psi), and stirred at 60° C. for 4 hours. The reaction was cooled to ambient temperature and concentrated under reduced pressure. The concentrate was purified by flash chromatography on silica gel, eluting with dichloromethane, to provide the title compound. MS ESI(+) m/z 562.0 [M+H]+.

Workup

temperatureThe reaction was cooled to ambient temperature
concentrationconcentrated under reduced pressure
customThe concentrate was purified by flash chromatography on silica gel
washeluting with dichloromethane

Sources & evidence

ORD record: ord-2c9522145e244c698cc9b289efced5e9
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08691810B2

Reaction notes

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