Cesium carbonate → HCID 90028433, compound

HRID 2200182Notes

Reaction equation

HRID 2200182 reaction equation
Br[C:2]1[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=1.[NH:15]1[CH2:20][CH2:19][S:18][CH2:17][CH2:16]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].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.O1CCOCC1>[N+:12]([C:4]1[CH:3]=[C:2]([N:15]2[CH2:20][CH2:19][S:18][CH2:17][CH2:16]2)[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=1)([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 10796Cesium carbonateHCID 67164ThiomorpholineHCID 70154111-Bromo-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 90028433HCID 90028433, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 634876Binap, (A+-)-CatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

Add 1-bromo-3-nitro-5-(trifluoromethyl)benzene (500 mg, 2.9 mmol), thiomorpholine (455 mg, 4.4 mmol), Cs2CO3 (2.86 g, 8.8 mmol), BINAP (55 mg, 0.09 mmol) and Pd2(dba)3 (54 mg, 0.06 mmol) under N2 to 1,4-dioxane (10 mL), stir the reaction under N2 at 100° C. for 16 hrs. TLC (100% PE) shows the reaction is complete. Cool the reaction to room temperature, filter and concentrate the filtrate under reduced pressure to get crude product. Purification by chromatography (silica gel, 100% PE) affords the target compound (475 mg, 55%). MS: (M+1): 293.1.

Workup

  1. customthe reaction under N2 at 100° C. for 16 hrs
  2. temperatureCool
  3. customthe reaction to room temperature
  4. filtrationfilter
  5. concentrationconcentrate the filtrate under reduced pressure
  6. customto get crude product
  7. customPurification by chromatography (silica gel, 100% PE)

Sources & evidence

ORD record
ord-c8e6c18572bd49baaee58168ae68d508
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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