Toluene → (+/-)-1-(3'-Methoxybiphenyl-4-yloxy)-4-(3-pyridyl)-2-butanol

HRID 1600962Notes

Reaction equation

C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.Br[C:26]1[CH:27]=[C:28]([CH:41]=[CH:42][CH:43]=1)[O:29][CH2:30][CH:31]([OH:40])[CH2:32][CH2:33][C:34]1[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=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.C(O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([C:43]2[CH:26]=[CH:27][C:28]([O:29][CH2:30][CH:31]([OH:40])[CH2:32][CH2:33][C:34]3[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=3)=[CH:41][CH:42]=2)[CH:19]=[CH:20][CH:21]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to the method as described in Example 33a) from toluene (8 ml), aqueous sodium carbonate (2 M, 2.47 ml), 3-methoxybenzeneboronic acid (0.413 g), ethanol (2 ml), (±)-1-(3-bromophenoxy)-4-(3-pyridyl)-2-butanol (0.79 g, Example 56a) and tetrakis(triphenylphosphine)palladium(0) (0.071 g) with heating at 120° C. for 4 hours. After work up the residue was purified by column chromatography over silica with ethyl acetate to give the title compound as a white solid after trituration with ether:hexane (0.27 g).

Workup

customPrepared
customAfter work up the residue was purified by column chromatography over silica with ethyl acetate

Sources & evidence

ORD record: ord-5ad339865b9b44d59b50af31e4abdc66
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977105

Reaction notes

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