Toluene → (3R,4S)-4-[4-(6-Dimethylaminopyridin-2-yl)phenoxy]-1-pyridin-3-ylpentan-3-ol

HRID 1856697Notes

Reaction equation

C1(C)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[Si]([O:21][C@H:22]([CH2:35][CH2:36][C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[C@H:23]([CH3:34])[O:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.[CH3:43][N:44]([C:46]1[CH:51]=[CH:50][CH:49]=[C:48](Br)[N:47]=1)[CH3:45]>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>[CH3:43][N:44]([CH3:45])[C:46]1[N:47]=[C:48]([C:28]2[CH:27]=[CH:26][C:25]([O:24][C@@H:23]([CH3:34])[C@H:22]([OH:21])[CH2:35][CH2:36][C:37]3[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=3)=[CH:30][CH:29]=2)[CH:49]=[CH:50][CH:51]=1

Participants

Conditions

Temperature: 120 °C

Procedure

Prepared according to the method described in Example 15g) from toluene (4 ml), 2M aqueous sodium carbonate (0.5 ml), (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-yl-butoxy]benzeneboronic acid (0.200 g, Example 15f)), ethanol (1 ml), 6-bromo-2-N,N-dimethylaminopyridine (0.201 g, Example 18a)) and tetrakis(triphenylphosphine)palladium(0) (0.020 g) with heating at 120° C. for 4 hours. The product was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give the title compound as an oil (0.091 g).

Workup

customPrepared
customThe product was purified by normal-phase HPLC
washeluting with a gradient of 0-25% ethanol in dichloromethane

Sources & evidence

ORD record: ord-55442c7a216145b2a2a14bb3b01f5363
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06143751

Reaction notes

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