Cesium carbonate → HCID 70981270, compound

HRID 1749073Notes

Reaction equation

HRID 1749073 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][NH:7][C:8]2[C:13]([N+:14]([O-:16])=[O:15])=[CH:12][CH:11]=[C:10](Cl)[N:9]=2)=[CH:4][CH:3]=1.[C:20]([O:24][C:25](=[O:33])[N:26]([C@H:28]([C:30](=[O:32])[NH2:31])[CH3:29])[CH3:27])([CH3:23])([CH3:22])[CH3:21].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O1CCOCC1>[C:20]([O:24][C:25](=[O:33])[N:26]([CH:28]([C:30](=[O:32])[NH:31][C:10]1[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:8]([NH:7][CH2:6][C:5]2[CH:18]=[CH:19][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)[CH3:29])[CH3:27])([CH3:21])([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 43330318HCID 43330318, compoundHCID 89157182HCID 89157182, compound2×

Product 1

HCID 70981270HCID 70981270, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

(4-Chloro-benzyl)-(6-chloro-3-nitro-pyridin-2-yl)-amine (685 mg, 2.31 mmol), ((S)-1-carbamoyl-ethyl)-methyl-carbamic acid tert-butyl ester (Intermediate A1) (606 mg, 3.0 mmol), Pd2 dba3 (210 mg, 0.23 mmol), BINAP (286 mg, 0.46 mmol) and Cs2CO3 (1.5 g, 4.62 mmol) were added to 1,4-dioxane (15 mL). The mixture was evacuated and flushed with N2 three times and then heated at 90° C. for 2 hours. The mixture was cooled, diluted with EtOAc, filtered and concentrated in vacuo. The residue was purified by SiO2 chromatography (10-30% EtOAc/Petrol) to give {1-[6-(4-chloro-benzylamino)-5-nitro-pyridin-2-ylcarbamoyl]-ethyl}-methyl-carbamic acid tert-butyl ester (611 mg) as an orange foamy solid. MS: [M+H]+=464.

Workup

  1. customThe mixture was evacuated
  2. customflushed with N2 three times
  3. temperatureThe mixture was cooled
  4. additiondiluted with EtOAc
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by SiO2 chromatography (10-30% EtOAc/Petrol)

Sources & evidence

ORD record
ord-5f5ba184f43c40028c6ba84ecaa893cf
Source dataset
uspto-grants-2015_10
Patent number
US09155743B2

Reaction notes

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