Tetrahydrofuran → HCID 86699031, compound

HRID 1424216Notes

Reaction equation

HRID 1424216 reaction equation
Br[C:2]1[CH:3]=[C:4]([NH2:10])[C:5]([NH2:9])=[CH:6][C:7]=1[F:8].[Br-].[CH2:12]([Zn+])[C:13]([CH3:16])([CH3:15])[CH3:14].O1CCCC1>C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC(P([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl.[Fe]>[F:8][C:7]1[CH:6]=[C:5]([NH2:9])[C:4]([NH2:10])=[CH:3][C:2]=1[CH2:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 199585604-Bromo-5-fluoro-1,2-benzenediamineHCID 178445880HCID 178445880, compound

Product 1

HCID 86699031HCID 86699031, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 178477754HCID 178477754, compoundCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 4-bromo-5-fluorobenzene-1,2-diamine (82.1 mg, 0.400 mmol), [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (20.2 mg, 0.0276 mmol), and neopentylzinc bromide in tetrahydrofuran (0.5 M, 3.0 mL, 1.5 mmol) was degassed for 5 minutes using argon. The reaction mixture was heated under microwave irradiation for 5 minutes at 140° C. The solution was concentrated in vacuo and purified by silica gel column chromatography eluting with 0-100% ethyl acetate/hexanes to afford the title compound (22 mg, 28%) as an orange oil.

Workup

  1. customwas degassed for 5 minutes
  2. concentrationThe solution was concentrated in vacuo
  3. custompurified by silica gel column chromatography
  4. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-1f4287e7bed24f44b8b95891119cf642
Source dataset
uspto-grants-2015_01
Patent number
US08927587B2

Reaction notes

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