Sodium Carbonate → HCID 58762771, compound

HRID 1453005Notes

Reaction equation

HRID 1453005 reaction equation
[CH3:1][C:2]1[S:6][C:5](B(O)O)=[CH:4][CH:3]=1.[Br:10][C:11]1[CH:16]=[CH:15][C:14](I)=[C:13]([F:18])[CH:12]=1.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>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([C:5]2[S:6][C:2]([CH3:1])=[CH:3][CH:4]=2)=[C:13]([F:18])[CH:12]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 27245164-Bromo-2-fluoro-1-iodobenzeneHCID 2734374(5-Methylthiophen-2-yl)boronic acid

Product 1

HCID 58762771HCID 58762771, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
75 °C

Procedure

A mixture of 5-methyl-2-thiophene-boronic acid (1 g, 7.0 mmol), 1-bromo-3-fluoro-4-iodobenzene (1.77 g, 5.9 mmol), tetrakis(triphenylphosphine)palladium(0) (0.34 g, 0.3 mmol), 2M Na2CO3 (10 mL) in DME (10 mL) was heated to 75° C. under N2 for 15 h. The reaction mixture was partitioned between 1N HCl and EtOAc. The organic layer was washed with saturated NaHCO3, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography (hexanes) to give the title compound (1.2 g, 75%). 1H NMR (CDCl3): δ 2.52 (s, 3H), 6.76 (s, 1H), 7.25-7.32 (m, 3H), 7.43 (t, 1H, J=8.5 Hz).

Workup

  1. customThe reaction mixture was partitioned between 1N HCl and EtOAc
  2. washThe organic layer was washed with saturated NaHCO3, brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was purified by silica gel chromatography (hexanes)

Sources & evidence

ORD record
ord-ecb0eb7a473543269024b5261c89a27f
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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