Benzaldehyde → HCID 67287111, compound

HRID 1626433Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[CH:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.B(O)(O)C1C=CC(C)=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[ClH:33].O1CCOCC1>C1(C)C=CC=CC=1.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>[ClH:33].[C:10]1([CH3:9])[CH:15]=[CH:14][C:13]([C:2]2[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=2)=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 6-bromopyridin-2-amine (0.500 g, 2.89 mmol) in toluene (10 ml) was added benzaldehyde (0.313 g, 2.95 mmol), and the reaction was stirred for 30 minutes. To this, p-tolylboronic acid (0.471 g, 3.47 mmol), sodium carbonate (0.368 g, 3.47 mmol), and water (10 ml) were added, and the reaction was degassed with argon. Tetrakis(triphenylphosphine)palladium (0.167 g, 0.144 mmol) was added, and the reaction was heated to 100° C. for 60 hours. The reaction was diluted with 10 ml of toluene and 10 ml of water, and the organic layer was collected. The organic layer was treated with 4M hydrogen chloride in dioxane (1.44 ml, 5.78 mmol) dropwise with vigorous stirring. The resulting solid was collected via filtration to yield pure 6-p-tolylpyridin-2-amine hydrochloride (0.564 g, 2.56 mmol, 88.4% yield).

Workup

customthe reaction was degassed with argon
customthe organic layer was collected
filtrationThe resulting solid was collected via filtration

Sources & evidence

ORD record: ord-0cbcf023e1174a2fb770afcec606b010
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785445B2

Reaction notes

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