Water → HCID 59564348, compound

HRID 2096257Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

4-(2-Bromophenyl)-piperazine-1-carboxylic acid, t-butyl ester (10 g, 29.30 mmol) and 2-methoxypyrimidine-5-boronic acid (5 g, 32.48 mmol) are dissolved in DMF (200 mL) under a stream of nitrogen. To this mixture is added a 2M aqueous solution of sodium carbonate (73.26 mL, 150 mmol) followed by bis(triphenylphosphine)palladium (II) chloride (2.06 g, 2.93 mmol). The resulting mixture is allowed to stir at 100° C. for 30 min. A precipitate forms. Water is added and the resulting mixture is filtered to provide a gray colored solid which is air dried. The solid is then re-dissolved in dichloromethane (20 mL) and loaded on a 340 g Biotage SNAP column and eluted with 35% ethyl acetate in hexanes to provide 4-[2-(2-methoxy-pyrimidin-5-yl)-phenyl]-piperazine-1-carboxylic acid t-butyl ester (5.87 g, 54% yield).

Workup

filtrationthe resulting mixture is filtered
customto provide a gray colored solid which
customdried
dissolutionThe solid is then re-dissolved in dichloromethane (20 mL)
washeluted with 35% ethyl acetate in hexanes

Sources & evidence

ORD record: ord-39822d8c39974375bacae3fde2673454
Source dataset: uspto-grants-2013_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08450317B2

Reaction notes

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