Ethanol → (3R,4S)-4-[4'-(2-Methylaminoethyl)biphenyl-4-yloxy]-1-pyridin-3-yl-pentan-3-ol

HRID 379994

Reaction equation

Cl.Br[C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][NH:11][CH3:12])=[CH:5][CH:4]=1.C(O)C.C(=O)([O-])[O-].[Na+].[Na+].[Si]([O:29][C@H:30]([CH2:43][CH2:44][C:45]1[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=1)[C@H:31]([CH3:42])[O:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][CH:34]=1)(C(C)(C)C)(C)C>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.C1(C)C=CC=CC=1>[CH3:12][NH:11][CH2:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([C:36]2[CH:35]=[CH:34][C:33]([O:32][C@@H:31]([CH3:42])[C@H:30]([OH:29])[CH2:43][CH2:44][C:45]3[CH:46]=[N:47][CH:48]=[CH:49][CH:50]=3)=[CH:38][CH:37]=2)=[CH:4][CH:5]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to the method described in Example 12b) from [2-(4-bromophenyl)ethyl]-N-methylamine hydrochloride (0.214 g, Example 30a)), ethanol (1 ml), toluene (4 ml), 2M aqueous sodium carbonate (0.5 ml), (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.2 g, Example 11)), and tetrakis(triphenylphosphine)palladium (0) (0.02 g) with heating at 120° C. for 4 hours. After work-up, the residue was purified by normal-phase HPLC eluting a gradient of 0-25% ethanol in dichloromethane to give the title compound as a pale yellow solid (0.081 g).

Workup

customPrepared
customAfter work-up, the residue was purified by normal-phase HPLC
washeluting a gradient of 0-25% ethanol in dichloromethane

Sources & evidence

ORD record: ord-b268e464118a4bb999441cb732a7040b
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06300352B1

Linked notes

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