Cesium carbonate → HCID 90032556, compound

HRID 2200174Notes

Reaction equation

HRID 2200174 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.C([O-])([O-])=O.[Cs+].[Cs+].[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]1.O1CCOCC1>CC([O-])=O.CC([O-])=O.[Pd+2].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.CO.C(Cl)Cl>[CH3:21][N:22]1[CH2:27][CH2:26][CH:25]([NH:28][C:2]2[CH:7]=[C:6]([C:8]([F:11])([F:10])[F:9])[CH:5]=[C:4]([N+:12]([O-:14])=[O:13])[CH:3]=2)[CH2:24][CH2:23]1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 27375314-Amino-1-methylpiperidineHCID 70154111-Bromo-3-nitro-5-(trifluoromethyl)benzene

Product 1

HCID 90032556HCID 90032556, compoundYield 102.1%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 634876Binap, (A+-)-CatalystHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

Add 1-bromo-3-nitro-5-(trifluoromethyl)benzene (3 g, 11.11 mmol), Cs2CO3 (9.5 g, 27.78 mmol), 1-methylpiperidin-4-amine (1.9 g, 16.67 mmol) to 1,4-dioxane (25 mL), then under N2, add Pd(OAc)2 (50 mg, 0.22 mmol) and BINAP (207 mg, 0.33 mmol). Stir the reaction at 120° C. under N2 overnight. TLC (DCM:MeOH=10:1) shows the reaction is complete. Cool to room temperature and filter off the solid. Concentrate the filtrate to get the crude product. Purification by chromatography (silica gel, DCM:MeOH-10:1) affords the title compound (3.44 g, 99%). MS: (M+1): 304.

Workup

  1. customthe reaction at 120° C. under N2 overnight
  2. filtrationfilter off the solid
  3. concentrationConcentrate the filtrate
  4. customto get the crude product
  5. customPurification by chromatography (silica gel, DCM:MeOH-10:1)

Sources & evidence

ORD record
ord-3c921d45d9db49a19aa44d9ff28fd715
Source dataset
uspto-grants-2016_06
Patent number
US09359338B2

Reaction notes

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