Sodium Carbonate → 4-Cyano-3-(2'-cyano-biphenyl-4-yl)-5-ethyl-thiophene-2-carboxylic acid ethyl ester

HRID 1990093Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:28][CH3:29])=[C:9]([C:26]#[N:27])[C:10]=1[C:11]1[CH:16]=[CH:15][C:14](B2OC(C)(C)C(C)(C)O2)=[CH:13][CH:12]=1)=[O:5])[CH3:2].I[C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[C:33]#[N:34].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CCOC(C)=O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([CH2:28][CH3:29])=[C:9]([C:26]#[N:27])[C:10]=1[C:11]1[CH:12]=[CH:13][C:14]([C:31]2[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=2[C:33]#[N:34])=[CH:15][CH:16]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

Prepare a solution of 4-cyano-5-ethyl-3-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-thiophene-2-carboxylic acid ethyl ester (0.26 mmol), 2-iodobenzonitrile (41 mg, 0.18 mmol), 2M aqueous Na2CO3 (0.6 mL, 1.2 mmol) and tetrakis(triphenylphosphine)-palladium(0) (20 mg, 0.02 mmol) in 3 mL of dioxane and heat to 80° C. under nitrogen. After 3 hours cool to room temperature, dilute with 50 mL of EtOAc and wash with water (2×10 mL) and brine (1×10 mL). Dry the organics over Na2SO4, filter and evaporate. Chromatograph on silica gel (100/0 to 3/1 toluene/EtOAc) to give the title compound as a yellow foam. Yield=61 mg (91%). HPLC=80%.

Workup

temperatureAfter 3 hours cool to room temperature
washwash with water (2×10 mL) and brine (1×10 mL)
dry with materialDry the organics over Na2SO4
filtrationfilter
customevaporate

Sources & evidence

ORD record: ord-18a81885bedf4c3392cfe33b540d3c13
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07642361B2

Reaction notes

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