Sodium Carbonate → HCID 86695028, compound

HRID 1468448Notes

Reaction equation

HRID 1468448 reaction equation
[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13](B2OC(C)(C)C(C)(C)O2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1.Br[C:28]1[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][N:29]=1.C(=O)([O-])[O-].[Na+].[Na+].C1COCC1.C1(C)C=CC=CC=1>C(OCC)(=O)C.Cl[Pd]Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C:5]1[C:14]([CH3:15])=[C:13]([C:28]2[CH:33]=[CH:32][C:31]([S:34]([CH3:37])(=[O:36])=[O:35])=[CH:30][N:29]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:25])[CH:11]=2)[CH:6]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 98994832-Bromo-5-(methylsulfonyl)pyridineHCID 22635083Tetrahydrofuran tolueneHCID 59350821[6-Fluoro-3-methyl-4-(4,4,5,5-tetra methyl-[1,3,2]-dioxaborolan-2-yl)-naphthalen-2-yl]-acetic acid methyl ester

Product 1

HCID 86695028HCID 86695028, compoundYield 10%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of [6-fluoro-3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-naphthalen-2-yl]-acetic acid methyl ester (0.130 g, 0.36 mmol), 2-bromo-5-methanesulfonylpyridine (0.086 g, 0.36 mmol), [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (0.005 g, 0.0068 mmol), and 1.0 M aqueous sodium carbonate (0.4 mL, 0.4 mmol) in 1:1 THF-toluene (4 mL) was heated at 80° C. for 20 hours. The reaction mixture was cooled to room temperature, and diluted with ethyl acetate. The resulting mixture was washed with water. The organic layer was dried (Na2SO4), filtered, and concentrated to give an oily yellow solid. Flash chromatography (40 g Analogix column, 5-60% ethyl acetate in hexanes) gave [6-fluoro-4-(5-methanesulfonyl-pyridin-2-yl)-3-methyl-naphthalen-2-yl]acetic acid methyl ester (0.014 g, 10%) as a solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 9.27 (d, J=3.00 Hz, 1 H), 8.49 (dd, J=8.00, 3.00 Hz, 1 H), 8.04 (dd, J=8.80, 6.60 Hz, 1 H), 7.97 (s, 1 H), 7.73 (d, J=9.00 Hz, 1 H), 7.41 (td, J=8.00, 3.20 Hz, 1 H), 6.72-6.78 (m, 1 H), 3.97-3.99 (m, 2 H), 3.65 (s, 3 H), 3.46 (s, 3 H), 2.05 (s, 3 H).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washThe resulting mixture was washed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give an oily yellow solid

Sources & evidence

ORD record
ord-5004fdc9872e4cca87c1bde48a3e9155
Source dataset
uspto-grants-2015_04
Patent number
US09000044B2

Reaction notes

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