Potassium Carbonate → 1,1-Dimethylethyl 4-{[3'-(aminomethyl)-3-biphenylyl]methyl}-1-piperazinecarboxylate

HRID 657370Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH2:8][NH2:9])[CH:5]=[CH:6][CH:7]=1.[CH3:10][C:11]([O:14][C:15]([N:17]1[CH2:22][CH2:21][N:20]([CH2:23][C:24]2[CH:25]=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=2)[CH2:19][CH2:18]1)=[O:16])([CH3:13])[CH3:12].C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd]>[NH2:9][CH2:8][C:4]1[CH:3]=[C:2]([C:26]2[CH:27]=[CH:28][CH:29]=[C:24]([CH2:23][N:20]3[CH2:21][CH2:22][N:17]([C:15]([O:14][C:11]([CH3:13])([CH3:12])[CH3:10])=[O:16])[CH2:18][CH2:19]3)[CH:25]=2)[CH:7]=[CH:6][CH:5]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a solution of [(3-bromophenyl)methyl]amine hydrochloric salt (0.556 g, 2.5 mmol) in 1,4-dioxane (15 mL) and H2O (5 mL) was added {3-[(4-{[(1,1-dimethylethyl)-oxy]carbonyl}-1-piperazinyl)methyl]phenyl}boronic acid (1.041 g, 3.25 mmol), Pd(PPH3)4 (0.144 g, 0.125 mmol), and K2CO3 (1.382 g, 10 mmol). This mixture was heated in a microwave oven at about 150° C. for about 15 mins. The organic layer was separated, dried using a Glas-Col evaporator (Sigma-Aldrich), and was then purified by CombiFlash chromatograph to afford the title compound 0.798 g (84%). LC-MS m/z 382 (M+H)+.

Workup

customThe organic layer was separated
customdried
customa Glas-Col evaporator (Sigma-Aldrich)
customwas then purified by CombiFlash chromatograph

Sources & evidence

ORD record: ord-d414c5951c6746da9afb3166a1c67849
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071588B2

Reaction notes

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