Cesium carbonate → HCID 118223446, compound

HRID 2200096Notes

Reaction equation

HRID 2200096 reaction equation
[NH2:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[N:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]([CH:16]3[CH2:18][CH2:17]3)=[O:15])[CH:8]=2)=C[C:3]=1C.C1(C([NH2:27])=O)CC1.C1(P(C2C=CC=CC=2)[C:35]2C=CC3[C:37](=CC=CC=3)[C:36]=2[C:45]2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:74]([O-:77])([O-])=[O:75].[Cs+].[Cs+]>O1CCOCC1.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]>[CH:16]1([C:14]([NH:13][C:9]2[N:10]=[CH:11][N:12]=[C:7]([O:6][C:5]3[N:27]=[CH:3][C:2]([NH:1][C:74](=[O:75])[O:77][C:36]([CH3:45])([CH3:37])[CH3:35])=[CH:20][CH:19]=3)[CH:8]=2)=[O:15])[CH2:17][CH2:18]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 80376CyclopropanecarboxamideHCID 634876Binap, (A+-)-HCID 90020675HCID 90020675, compound

Product 1

HCID 118223446HCID 118223446, compoundYield 708.6%

Reagents, catalysts & solvents 2

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

Procedure

Mix the compound obtained in Step 2 (610 mg, 1.9 mmol), cyclopropanecarboxamide (193 mg, 2.27 mmol), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (BINAP, 118 mg, 0.19 mmol), Cs2CO3 (1.238 g, 3.8 mmol) and tris(dibenzylideneacetone)dipalladium [Pd2(dba)3, 122 mg, 0.133 mmol] in 1,4-dioxane (30 mL). Stir the reaction at 120° C. under N2 for 16 hrs. Cool the reaction, filter, concentrate the filtrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=1:1) affords the title compound (500 mg, 70.8%). MS: (M+1): 372.2.

Workup

  1. customthe reaction at 120° C. under N2 for 16 hrs
  2. temperatureCool
  3. customthe reaction
  4. filtrationfilter
  5. concentrationconcentrate the filtrate under reduced pressure
  6. customto give the crude product
  7. customPurification by chromatography (silica gel, EtOAc:PE=1:1)

Sources & evidence

ORD record
ord-d4ab1ceb2f4640229808f01c7a69faaa
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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