Sodium Carbonate → HCID 59318163, compound

HRID 2190535Notes

Reaction equation

HRID 2190535 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[C:4]([F:9])[CH:3]=1.[F:10][C:11]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=1B(O)O.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.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>[F:9][C:4]1[CH:3]=[C:2]([C:14]2[CH:13]=[CH:12][C:11]([F:10])=[CH:16][C:15]=2[F:17])[CH:7]=[CH:6][C:5]=1[NH2:8]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 1230504-Bromo-2-fluoroanilineHCID 27343342,4-Difluorophenylboronic acid

Product 1

HCID 59318163HCID 59318163, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 4-bromo-2-fluoro-phenylamine (190 mg, 1 mmol) and 2,4-difluorophenylboronic acid (240 mg, 1 mmol) in 2.5 ml of 1,2-dimethoxy-ethane was added tetrakis(triphenylphosphine)palladium(0) (110 mg, 0.1 mmol) and 0.5 ml of 2M sodium carbonate aqueous solution. The mixture was microwaved at 150° C. for 15 min. The solvents were evaporated and the residue was diluted with CH2Cl2 and filtered. The filtration was concentrated and purified on a flash chromatography column with 0-80% EtOAc/hexanes to give 3,2′,4′-trifluoro-biphenyl-4-ylamine as an off-white solid (200 mg, 90%). LRMS calcd for C12H8F3N (m/e) 223, obsd 224 (M+H).

Workup

  1. customThe mixture was microwaved at 150° C. for 15 min
  2. customThe solvents were evaporated
  3. additionthe residue was diluted with CH2Cl2
  4. filtrationfiltered
  5. filtrationThe filtration
  6. concentrationwas concentrated
  7. custompurified on a flash chromatography column with 0-80% EtOAc/hexanes

Sources & evidence

ORD record
ord-4afd343b053f40fba807a725f8197770
Source dataset
uspto-grants-2012_12
Patent number
US08324385B2

Reaction notes

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