Sodium Carbonate → HCID 67997358, compound

HRID 470392Notes

Reaction equation

Br[C:2]1[C:3]([S:8][CH2:9][C:10]([O:12]C)=[O:11])=[N:4][CH:5]=[N:6][CH:7]=1.CC1(C)C(C)(C)OB([C:22]2[C:31]3[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:25]([C:32]#[N:33])=[CH:24][CH:23]=2)O1.C(=O)([O-])[O-].[Na+].[Na+].[OH-].[Na+]>O1CCOCC1>[C:32]([C:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:22]([C:2]2[C:3]([S:8][CH2:9][C:10]([OH:12])=[O:11])=[N:4][CH:5]=[N:6][CH:7]=2)=[CH:23][CH:24]=1)#[N:33]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of methyl 2-(5-bromopyrimidin-4-ylthio)acetate (220 mg, 0.84 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-naphthonitrile (237 mg, 0.85 mmol) palladium tetrakis triphenylphoshine (46 mg, 0.04 mmol) and aqueous sodium carbonate solution (2M, 1.5 mL, 3 mmol) in dioxane (3 mL) was heated to 100° C. for 5 hours. The reaction mixture was allowed to cool to room temperature and aqueous sodium hydroxide solution added (1M, 30 mL). The mixture was washed with ethyl acetate (2×20 mL), and the aqueous layer acidified to pH 4 resulting in formation of a precipitate which was isolated by filtration and dried under vacuum to yield 2-(5-(4-cyanonaphthalen-1-yl)pyrimidin-4-ylthio)acetic acid (143 mg, 53%).

Workup

temperatureto cool to room temperature
washThe mixture was washed with ethyl acetate (2×20 mL)
customresulting in formation of a precipitate which
customwas isolated by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-d60a26cff6d84c62ae64d0427a7577b2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629278B2

Reaction notes

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