Potassium Carbonate → HCID 18451504, compound

HRID 1270737Notes

Reaction equation

HRID 1270737 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7](Br)[C:6]([CH:10]2[CH2:12][CH2:11]2)=[C:5]([F:13])[C:3]=1[NH2:4].[CH3:14]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:8]=[C:7]([CH3:14])[C:6]([CH:10]2[CH2:12][CH2:11]2)=[C:5]([F:13])[C:3]=1[NH2:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 18451498HCID 18451498, compound

Product 1

HCID 18451504HCID 18451504, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Procedure

2-Chloro-4-bromo-5-cyclopropyl-6-fluoroaniline (14.0 g, 53 mmol), trimethylboroxine (13.4 g of 50% solution in THF, 53 mmol), tetrakis(triphenylphosphine)palladium(0) (2.5 g, 2.2 mmol) and potassium carbonate (14.0 g, 101 mmol) are combined and stirred in 250 mL of a 4:1 DME/water solution. The mixture is degassed by repeated alternating application of vacuum and positive nitrogen pressure (10×). The mixture is heated to reflux temperature for 2 days and then cooled to room temperature. Most of the DME is removed by rotary evaporator and the residual mixture is partitioned between Et2O (500 mL) and water (500 mL). The organic phase is washed with brine (3×250 mL), dried (MgSO4) and concentrated by rotary evaporator. The crude product is purified using flash chromatography (5% CH2Cl2/hexanes) to give 2-chloro-4-methyl-5-cyclopropyl-6-fluoroaniline a light yellow oil.

Workup

  1. customThe mixture is degassed by repeated alternating application of vacuum and positive nitrogen pressure (10×)
  2. temperatureThe mixture is heated
  3. temperatureto reflux temperature for 2 days
  4. customMost of the DME is removed by rotary evaporator
  5. customthe residual mixture is partitioned between Et2O (500 mL) and water (500 mL)
  6. washThe organic phase is washed with brine (3×250 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated by rotary evaporator
  9. customThe crude product is purified

Sources & evidence

ORD record
ord-3c986cdba4e745a793b302c67aa1c2e9
Source dataset
uspto-grants-2007_04
Patent number
US07202364B2

Reaction notes

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