Cesium carbonate → HCID 58449365, compound

HRID 2278720Notes

Reaction equation

HRID 2278720 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=2)[CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].[NH:19]1[CH2:24][CH2:23][O:22][CH2:21][C:20]1=[O:25].C(=O)([O-])[O-].[Cs+].[Cs+].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)C.[Pd+2].C([O-])(=O)C.O1CCOCC1>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([C:10]2[CH:9]=[C:4]([CH:3]=[C:2]([N:19]3[CH2:24][CH2:23][O:22][CH2:21][C:20]3=[O:25])[CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[N:13][CH:14]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 669533-MorpholinoneHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59599704Methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate

Product 1

HCID 58449365HCID 58449365, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent

Procedure

A microwave vial was charged with methyl 3-bromo-5-(5-methylpyridin-2-yl)benzoate (100 mg, 0.33 mmol), morpholin-3-one (42 mg, 0.41 mmol), palladium acetate (4 mg), cesium carbonate (169 mg, 0.52 mmol), xantphos (3 mg), and 1,4-dioxane (1 mL). The reaction mixture was subjected to microwave irradiation at 110° C. for 15 min. The reaction mixture was filtered and the filterate was concentrated under reduced pressure. The resultant residue was purified by preparative HPLC to get the product as a yellow solid.

Workup

  1. customirradiation at 110° C. for 15 min
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filterate was concentrated under reduced pressure
  4. customThe resultant residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-4615cd8a1a5c400fba75b91bc57d9c20
Source dataset
uspto-grants-2015_09
Patent number
US09133122B2

Reaction notes

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