1,2-Dimethoxyethane → Ethyl 5-(3-fluorobenzyl)isoxazole-3-carboxylate

HRID 58528Notes

Reaction equation

HRID 58528 reaction equation
COCCOC.Br[CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=1.[F:19][C:20]1[CH:21]=[C:22](B(O)O)[CH:23]=[CH:24][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+]>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.O>[F:19][C:20]1[CH:25]=[C:24]([CH:23]=[CH:22][CH:21]=1)[CH2:8][C:9]1[O:13][N:12]=[C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:10]=1

Participants

7

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 27339863-Fluorophenylboronic acidHCID 13124955Ethyl 5-(bromomethyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 66831768Ethyl 5-(3-fluorobenzyl)isoxazole-3-carboxylateYield 61%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

1,2-Dimethoxyethane (8 mL) and water (2 mL) were added to the mixture of ethyl 5-(bromomethyl)isoxazole-3-carboxylate (0.710 g; 3.03 mmol), 3-fluorophenylboronic acid (0.481 g; 3.34 mmol), tetrakis(triphenylphosphine)palladium(0) (0.176 g; 0.151 mmol) and sodium carbonate (0.646 g, 6.07 mmol). The mixture was irradiated in a microwave oven at 130° C. for 15 min and was evaporated. The residue was partitioned between dichloromethane (30 mL) and brine (20 mL). The organic layer was separated and concentrated. The residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane) to afford 0.460 g (61%) of ethyl 5-(3-fluorobenzyl)isoxazole-3-carboxylate as a yellow oil.

Workup

  1. customThe mixture was irradiated in a microwave oven at 130° C. for 15 min
  2. customwas evaporated
  3. customThe residue was partitioned between dichloromethane (30 mL) and brine (20 mL)
  4. customThe organic layer was separated
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica gel (eluent: 15 to 100% of dichloromethane in heptane)

Sources & evidence

ORD record
ord-c6d7ad25266249bcbbaeda1339e3ffb8
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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