Cesium carbonate → Benzyl 4-(2-methoxypyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate

HRID 572423Notes

Reaction equation

HRID 572423 reaction equation
[O:1]=[C:2]1[NH:7][CH:6]2[CH:4]([CH2:5]2)[N:3]1[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9].Br[C:19]1[CH:24]=[CH:23][N:22]=[C:21]([O:25][CH3:26])[CH:20]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.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>[CH3:26][O:25][C:21]1[CH:20]=[C:19]([N:7]2[CH:6]3[CH:4]([CH2:5]3)[N:3]([C:8]([O:10][CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[O:9])[C:2]2=[O:1])[CH:24]=[CH:23][N:22]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2802741Benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylateHCID 140623094-Bromo-2-methoxypyridine

Product 1

HCID 70982767Benzyl 4-(2-methoxypyridin-4-yl)-3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylateYield 41.1%

Reagents, catalysts & solvents 2

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

Procedure

Using analogous reagents and reaction conditions as described in Example 1 above, benzyl 3-oxo-2,4-diazabicyclo[3.1.0]hexane-2-carboxylate (50 mg, 0.215 mmol) was reacted with 4-bromo-2-methoxypyridine (44.5 mg, 0.237 mmol), xantphos (11 mg, 0.019 mmol), Pd2(dba)3 (6.0 mg, 0.006 mmol), cesium carbonate (105 mg, 0.32 mmol) and 1,4-dioxane (3.0 mL) in seal tube at 100° C. for 2.5 hours. Purification by column chromatography on silica gel (50% ethyl acetate in hexane) afforded (35% ethyl acetate in hexane) afforded 30 mg of the product (41% yield).

Workup

  1. customreagents and reaction conditions
  2. customPurification by column chromatography on silica gel (50% ethyl acetate in hexane)
  3. customafforded (35% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b6df9bc14116408a8b515ffe85d95b35
Source dataset
uspto-grants-2015_05
Patent number
US09029399B2

Reaction notes

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