Isobutylamine → Ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate

HRID 906187Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[C:13]#[N:14])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:15][CH:16]([CH3:19])[CH2:17][NH2:18].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[C:13]([C:12]1[CH:11]=[CH:10][C:4]([C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:3][C:2]=1[NH:18][CH2:17][CH:16]([CH3:19])[CH3:15])#[N:14]

Participants

Conditions

Temperature: 95 °C

Procedure

A mixture of ethyl 3-bromo-4-cyanobenzoate (500 mg, 2.08 mmol), 2-methylpropan-1-amine (250 μL, 4.16 mmol), Pd2(dba)3 (96 mg, 5 mol %), Xantphos (120 mg, 10 mol %) and potassium phosphate (959 mg, 4.16 mmol) in dioxane (10 mL) was stirred for overnight at 95° C. After cooling to room temperature the mixture was diluted with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated followed by column chromatography (10% ethyl acetate in hexanes) to give ethyl 4-cyano-3-[(2-methylpropylamino)]benzoate (393 mg, 76.7%) as a yellow solid. 1MS (EI) for C14H18N2O2: 247.1 (MH+).

Workup

temperatureAfter cooling to room temperature the mixture
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
filtrationfiltered
concentrationconcentrated

Sources & evidence

ORD record: ord-893de11e4b9e48e6a28b510f3b5248e1
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012956B2

Reaction notes

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