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

HRID 564550Notes

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]([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>[NH2:9][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), K2CO3 (1.382 g, 10 mmol) and was heated in a microwave at 150° C. for 15 min. The organic layer was separated, dried with a Glas-Col evaporator, then was purified by CombiFlash chromatograph to afford 0.798 g (84%) of the title compound. LC-MS m/z 382 (M+H)+.

Workup

customThe organic layer was separated
customdried with a Glas-Col evaporator
customwas purified by CombiFlash chromatograph

Sources & evidence

ORD record: ord-d37c9c7bab6e49d6a0de92f857ca58ac
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067408B2

Reaction notes

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