Sodium Carbonate → HCID 42629074, compound

HRID 332274Notes

Reaction equation

HRID 332274 reaction equation
Br[C:2]1[C:3]([O:17][CH2:18][C:19]2[C:20]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[N:21][O:22][C:23]=2[CH3:24])=[N:4][CH:5]=[C:6]([CH:16]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:8].[CH3:31]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.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>[CH3:31][C:2]1[C:3]([O:17][CH2:18][C:19]2[C:20]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[N:21][O:22][C:23]=2[CH3:24])=[N:4][CH:5]=[C:6]([CH:16]=1)[C:7]([NH:9][CH:10]1[CH2:15][CH2:14][O:13][CH2:12][CH2:11]1)=[O:8]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 574072TrimethylboroxineHCID 68442799HCID 68442799, compound

Product 1

HCID 42629074HCID 42629074, compoundYield 50.8%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 5-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-N-(tetrahydro-pyran-4-yl)-nicotinamide (200 mg, 0.42 mmol) in 1,2-dimethoxyethane (1 mL) was added trimethylboroxine (88 μL, 0.64 mmol), aqueous sodium carbonate (1 M, 0.64 mL, 0.64 mmol) and tetrakis(triphenylphosphine)palladium(0) (49 mg, 0.04 mmol). The reaction mixture was then irradiated in the microwave for 20 min at 140° C. under an argon atmosphere. It was diluted with ethyl acetate (10 mL) and washed with water (10 mL) and brine (10 mL). The aqueous layers were extracted with ethyl acetate (10 mL) and the combined organic layers were dried over sodium sulfate. Trituration from tert-butylmethylether afforded the title compound (87 mg, 50%) which was obtained as a white solid. MS: m/e=408.4 [M+H]+

Workup

  1. customThe reaction mixture was then irradiated in the microwave for 20 min at 140° C. under an argon atmosphere
  2. washwashed with water (10 mL) and brine (10 mL)
  3. extractionThe aqueous layers were extracted with ethyl acetate (10 mL)
  4. dry with materialthe combined organic layers were dried over sodium sulfate

Sources & evidence

ORD record
ord-1096c6d1a8144dd79e2206cd53bdc919
Source dataset
uspto-grants-2014_11
Patent number
US08877783B2

Reaction notes

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