Cesium carbonate → HCID 86708670, compound

HRID 921779Notes

Reaction equation

HRID 921779 reaction equation
Br[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([Cl:27])[CH:3]=1.[CH3:28][NH:29][CH2:30][CH2:31][NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].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]>[C:35]([O:34][C:33]([NH:32][CH2:31][CH2:30][N:29]([CH3:28])[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([N:10]([CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[C:4]([Cl:27])[CH:3]=1)=[O:39])([CH3:38])([CH3:37])[CH3:36]

Participants

6

Reactant 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 3435744N-(tert-Butoxycarbonyl)-N'-methylethylenediamineHCID 86708669HCID 86708669, compound

Product 1

HCID 86708670HCID 86708670, compoundYield 90.7%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl (4-bromo-2-chloro-5-cyanophenyl)(4-methoxybenzyl)carbamate (363 mg, 0.803 mmol), tert-butyl (2-(methylamino)ethyl)carbamate (182 mg, 1.05 mmol), Pd2(dba)3 (51.5 mg, 0.056 mmol), BINAP (105 mg, 0.169 mmol), and Cs2CO3 (524 mg, 1.61 mmol) in a dry microwave vial was flushed with nitrogen. Toluene (5 mL) was added and the vial was sealed and heated at 100° C. overnight. The reaction was diluted with EtOAc and filtered through celite. The solvent was removed from the filtrate and silica gel radial chromatography eluting with hexane containing 5 to 30% EtOAc afforded tert-butyl (4-((2-((tert-butoxycarbonyl)amino)ethyl)(methyl)amino)-2-chloro-5-cyanophenyl)(4-methoxybenzyl)carbamate (397 mg) as an oil.

Workup

  1. customwas flushed with nitrogen
  2. additionToluene (5 mL) was added
  3. customthe vial was sealed
  4. additionThe reaction was diluted with EtOAc
  5. filtrationfiltered through celite
  6. customThe solvent was removed from the filtrate and silica gel radial chromatography
  7. washeluting with hexane containing 5 to 30% EtOAc

Sources & evidence

ORD record
ord-cafad5e70f844b3690df85ae24f9b284
Source dataset
uspto-grants-2016_03
Patent number
US09273057B2

Reaction notes

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