Cesium carbonate → HCID 86690970, compound

HRID 1055697Notes

Reaction equation

HRID 1055697 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5]([O:7][CH3:8])=[O:6].Cl.[F:13][C:14]1([F:20])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:13][C:14]1([F:20])[CH2:19][CH2:18][N:17]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][CH:11]=2)[C:5]([O:7][CH3:8])=[O:6])[CH2:16][CH2:15]1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 12070Methyl 3-bromobenzoateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 27583514,4-Difluoropiperidine hydrochloride

Product 1

HCID 86690970HCID 86690970, compound

Reagents, catalysts & solvents 2

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

Conditions

Temperature
130 °C

Procedure

In a microwave reaction vessel, a solution of 500 mg (2.33 mmol) of methyl 3-bromobenzoate and 366 mg (2.33 mmol) of 4,4-difluoropiperidine hydrochloride in 15 ml of dioxane was deoxygenated by passing through argon. 52 mg (0.233 mmol) of palladium(II) acetate, 202 mg (0.349 mmol) of 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xantphos) and 2.27 g (6.98 mmol) of caesium carbonate were then added. The microwave vessel was closed with a crimp closure and, with magnetic stirring, heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 120-140° C. for 1.5 hours. After the reaction had ended the reaction mixture was filtered through a little kieselguhr and then evaporated to dryness. The residue was separated into its components by preparative HPLC (Method 33). Evaporation of the product fractions and drying of the residue under high vacuum gave 342 mg (57% of theory) of the title compound.

Workup

  1. customIn a microwave reaction vessel
  2. customThe microwave vessel was closed with a crimp closure and, with magnetic stirring
  3. filtrationwas filtered through a little kieselguhr
  4. customevaporated to dryness
  5. customThe residue was separated into its components by preparative HPLC (Method 33)
  6. customEvaporation of the product fractions
  7. customdrying of the residue under high vacuum

Sources & evidence

ORD record
ord-cfdda3d0003446b8863a505fb26a9bfa
Source dataset
uspto-grants-2016_07
Patent number
US09394309B2

Reaction notes

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