Dimethylacetamide → HCID 86689782, compound

HRID 1396439Notes

Reaction equation

HRID 1396439 reaction equation
Br[C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]([N+:10]([O-:12])=[O:11])[N:3]=1.[CH3:13][C:14]1(C)[C:18](C)(C)OB(C(C)=C)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CC(N(C)C)=O>C(OCC)(=O)C.[Cl-].[Na+].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.O>[CH3:9][O:8][C:7]1[C:2]([C:14]([CH3:18])=[CH2:13])=[N:3][C:4]([N+:10]([O-:12])=[O:11])=[CH:5][CH:6]=1

Participants

9

Reactant 4

HCID 31374DimethylacetamideHCID 62657Potassium Phosphate, TribasicHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 126928732-Bromo-3-methoxy-6-nitropyridine

Product 1

HCID 86689782HCID 86689782, compoundYield 66%

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
150 °C

Procedure

In a microwave vial was added a mixture of 2-bromo-3-methoxy-6-nitropyridine (1.5 g, 6.44 mmol), 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.41 g, 8.37 mmol), tetrakis(triphenylphosphine)palladium (0) (744 mg, 644 μmol), potassium phosphate tribasic (2.73 g, 12.9 mmol), DMA (16.1 mL) and water (5.36 mL). The vial was sealed and heated in the microwave for 20 min at 150° C., then cooled and diluted with ethyl acetate and brine. The organic phase was separated and washed with brine (3×), then concentrated in vacuo and purified by chromatography (silica, 5 to 35% ethyl acetate in hexanes) to give 3-methoxy-6-nitro-2-(prop-1-en-2-yl)pyridine (824 mg, 4.24 mmol, 66%) as a brown solid. MS (EI/CI) m/z: 194.8 [M+H].

Workup

  1. additionIn a microwave vial was added
  2. customThe vial was sealed
  3. temperaturecooled
  4. customThe organic phase was separated
  5. washwashed with brine (3×)
  6. concentrationconcentrated in vacuo
  7. custompurified by chromatography (silica, 5 to 35% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-f2a2c516226e40c7a6f7298e2ffe513b
Source dataset
uspto-grants-2014_12
Patent number
US08901124B2

Reaction notes

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