Tetrahydrofuran → HCID 11992566, compound

HRID 2241040Notes

Reaction equation

HRID 2241040 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[C:9]2[CH2:14][C:13]([CH3:16])([CH3:15])[CH2:12][C:11]([CH3:18])([CH3:17])[CH2:10]2)=[CH:4][CH:3]=1.[CH3:25][C:26]1[C:30](B(O)O)=[C:29]([CH3:34])[O:28][N:27]=1.C([O-])([O-])=O.[Na+].[Na+].C1COCC1>CCOC(C)=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>[CH3:25][C:26]1[C:30]([C:2]2[CH:3]=[CH:4][C:5]([C:8]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)=[C:9]3[CH2:10][C:11]([CH3:18])([CH3:17])[CH2:12][C:13]([CH3:15])([CH3:16])[CH2:14]3)=[CH:6][CH:7]=2)=[C:29]([CH3:34])[O:28][N:27]=1

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 68501670HCID 68501670, compound

Product 1

HCID 11992566HCID 11992566, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

An round-bottomed flask was charged with 16 (192 mg, 0.5 mmol), Pd(Ph3P)4 (58 mg, 0.05 mmol), (3,5-dimethyl-4-isoxazolyl)boronic acid (141 mg, 1.0 mmol), 2 N aqueous Na2CO3 (0.5 mL, 1 mmol), and THF (5 mL). The reaction mixture was refluxed for 18 h. The mixture was cooled to RT, diluted with EtOAc (100 mL), and then the mixture was washed with H2O (1×25 mL), brine (1×25 mL), dried over Na2SO4, filtered, and concentrated under reduced pressure to afford the crude product, which was purified by flash column chromatography to give 136 mg (68%) of the title product 22 as a white solid. 1H NMR (400 MHz, CDCl3): δ 0.94 (s, 6H), 0.97 (s, 6H), 1.31 (s, 2H), 1.97 (s, 2H), 2.01 (s, 2H), 2.28 (s, 3H), 2.41 (s, 3H), 7.32-7.14 (m, 9H). LCMS (APCI): m/z 400 (M+H)+.

Workup

  1. temperatureThe reaction mixture was refluxed for 18 h
  2. washthe mixture was washed with H2O (1×25 mL), brine (1×25 mL)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford the crude product, which
  7. customwas purified by flash column chromatography

Sources & evidence

ORD record
ord-eb4e00455ffc4c01854d918bc5ff8150
Source dataset
uspto-grants-2010_05
Patent number
US07723393B2

Reaction notes

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