3-Aminophenylboronic acid → [7-(3-Amino-phenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine

HRID 983486Notes

Reaction equation

Br[C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([N:12]([CH2:16][CH:17]3[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:19][CH2:18]3)[CH2:13][CH2:14][CH3:15])[CH2:9]2)=[CH:4][CH:3]=1.[NH2:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=1>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.[OH-].[Na+]>[NH2:27][C:28]1[CH:33]=[C:32]([C:4]2[CH:5]=[C:6]3[C:11]([CH2:10][CH2:9][CH:8]([N:12]([CH2:16][CH:17]4[CH2:22][CH2:21][N:20]([S:23]([CH3:26])(=[O:25])=[O:24])[CH2:19][CH2:18]4)[CH2:13][CH2:14][CH3:15])[CH2:7]3)=[CH:2][CH:3]=2)[CH:31]=[CH:30][CH:29]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 1 mL solution of (7-bromo-1,2,3,4-tetrahydro-naphthalen-2-yl)-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine (25 mmole in DMA) was added to a tube containing 2-3 mg Pd(PPh3)4 catalyst followed by 120 μL of a solution of 3-amino phenyl boronic acid (30 mmole in DMA), and 200 μL 1N aq. NaOH. The solution was shaken at 80° C. for 4 h, concentrated, and purified by chromatography to yield [7-(3-amino-phenyl)-1,2,3,4-tetrahydro-naphthalen-2-yl]-(1-methanesulfonyl-piperidin-4-ylmethyl)-propyl-amine 112[M+H]+=456.

Workup

concentrationconcentrated
custompurified by chromatography

Sources & evidence

ORD record: ord-0eca83efcb214c41a2b7b0a38e5e4399
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06864266B2

Reaction notes

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