Potassium Carbonate → (S)-tert-butyl 1-cyano-2-(3'-cyanobiphenyl-4-yl)ethylcarbamate

HRID 600293Notes

Reaction equation

[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[CH:7][CH:8]=1)#[N:2].[C:12]([C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH2:15][C:16]1[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=1)#[N:13].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.[Cl-].[Na+].O>[C:12]([C@@H:14]([NH:23][C:24](=[O:30])[O:25][C:26]([CH3:28])([CH3:27])[CH3:29])[CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:1]#[N:2])[CH:4]=2)=[CH:18][CH:17]=1)#[N:13]

Participants

Conditions

Temperature: 75 °C

Procedure

A solution of 3-cyanophenylboronic acid (4.74 g), (S)-tert-butyl 1-cyano-2-(4-iodophenyl)ethylcarbamate (10 g) and bis[bis(1,2-diphenylphosphino)-ethane]palladium (0) (0.243 g) in dioxane (100 mL) under nitrogen, was stirred for 10 min. A solution of potassium carbonate (7.43 g) in water (30 mL) was added and the resulting solution was stirred at 75° C. for 3 h. The cooled mixture was poured into water containing brine and extracted with ethyl acetate (3×150 mL). The combined organics were washed with saturated brine (3×50 mL), dried over sodium sulfate and adsorbed onto silica. The crude product was purified by flash silica chromatography, eluting with 20% ethyl acetate in isohexane. Pure fractions were evaporated to dryness to afford (S)-tert-butyl 1-cyano-2-(3′-cyanobiphenyl-4-yl)ethylcarbamate (8.42 g) as a pale yellow solid.

Workup

extractionextracted with ethyl acetate (3×150 mL)
washThe combined organics were washed with saturated brine (3×50 mL)
dry with materialdried over sodium sulfate
customThe crude product was purified by flash silica chromatography
washeluting with 20% ethyl acetate in isohexane
customPure fractions were evaporated to dryness

Sources & evidence

ORD record: ord-5e2ea4f11b1a492c822d78036c4699b7
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07902181B2

Reaction notes

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