4-(Tetramethyl-1,3,2-dioxaborolan-2-yl)aniline → Methyl 4-(4'-amino-[1,1'-biphenyl]-4-yl)butanoate

HRID 1944862Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][CH:10]=2)O1.I[C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=1.C(Cl)Cl.CO>C(COC)OC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:13][C:12]1[CH:11]=[CH:10][C:9]([C:18]2[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH3:30])=[O:28])=[CH:20][CH:19]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

Solid 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (158 mg, 0.723 mmol) and Pd(PPh3)4 (38 mg, 0.033 mmol) were added to a solution of methyl 4-(4-iodophenyl)butanoate (200 mg, 0.657 mmol) in dimethoxyethane/2M Na2CO3 (3 mL, 2:1) at rt. The resulting mixture was degassed with argon gas then heated at 110° C. using microwave for 30 min. The reaction mixture was diluted with EtOAc (10 mL) then washed with H2O (10 mL), brine (10 mL), dried over Na2SO4, and concentrated to give crude (294 mg) as brown oil. Chromatography (9:1, CH2Cl2/MeOH) afforded the title compound (146 mg, 82%) as a light yellow solid. ES/MS calcd. for C17H20NO2+ 270.2. Found m/z=270.2 (M+H)+.

Workup

customThe resulting mixture was degassed with argon gas
customfor 30 min
additionThe reaction mixture was diluted with EtOAc (10 mL)
washthen washed with H2O (10 mL), brine (10 mL)
dry with materialdried over Na2SO4
concentrationconcentrated
customto give crude (294 mg) as brown oil

Sources & evidence

ORD record: ord-b142cb6eb8514a8ba655f3f9bdac79a3
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394829B2

Reaction notes

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