Acetonitrile → Propanoic acid, 2-[[3-(4-cyanophenyl)-4-pyridinyl]thio]-2-methyl-, ethyl ester

HRID 470380Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1)#[N:2].Br[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][C:18]=1[S:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23][CH2:24][CH3:25])=[O:22].C(#N)C.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:17]2[CH:16]=[N:15][CH:14]=[CH:13][C:18]=2[S:19][C:20]([CH3:26])([CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:5][CH:4]=1)#[N:2]

Participants

Conditions

Temperature: 150 °C

Procedure

To a mixture of 4-cyanophenylboronic acid (49 mg, 0.33 mmol) and Pd(dppf)Cl2 (9 mg, 5% mole) were added a solution of freshly purified ethyl 2-(3-bromopyridin-4-ylthio)-2-methylpropanoate from (step B, 67 mg, 0.22 mmol) in THF (1 mL), acetonitrile (0.5 mL), and sodium carbonate (1M aqueous, 0.5 mL). The resulting mixture was degassed by nitrogen bubbling for 1 minute, and then heated to 150° C. for 30 minutes under microwave irradiation. The mixture was loaded on to a 5 g ISCO loading cartridge and eluded with a gradient of 0-100% ethyl acetate in hexane on a 12 g ISCO column to yield ethyl 2-(3-(4-cyanophenyl)pyridin-4-ylthio)-2-methylpropanoate (0.049 g, 70%).

Workup

customThe resulting mixture was degassed by nitrogen bubbling for 1 minute

Sources & evidence

ORD record: ord-bb22b61748a741a6aa2025a65dd6b343
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629278B2

Reaction notes

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