Sodium Carbonate → (S)-5,5-dimethyl-4-phenyl-3-(4-(7-(pyrimidin-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl)oxazolidin-2-one

HRID 525378Notes

Reaction equation

HRID 525378 reaction equation
I[C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C@@H:21]([C:22]5[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=5)[C:20]([CH3:29])([CH3:28])[O:19][C:18]4=[O:30])=[CH:13][CH:12]=3)=[N:9][N:10]=[C:4]2[CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[N:37]1[CH:42]=[C:41](B(O)O)[CH:40]=[N:39][CH:38]=1>O1CCOCC1>[CH3:28][C:20]1([CH3:29])[O:19][C:18](=[O:30])[N:17]([C:14]2[CH:15]=[CH:16][C:11]([C:8]3[N:5]4[CH:6]=[CH:7][C:2]([C:41]5[CH:42]=[N:37][CH:38]=[N:39][CH:40]=5)=[CH:3][C:4]4=[N:10][N:9]=3)=[CH:12][CH:13]=2)[C@H:21]1[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 89815193(S)-3-(4-(7-Iodo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one

Product 1

HCID 89815367(S)-5,5-dimethyl-4-phenyl-3-(4-(7-(pyrimidin-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
130 °C

Procedure

(S)-3-(4-(7-Iodo-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (70 mg, 0.137 mmol), sodium carbonate (2 M, 137 μL, 0.274 mmol), 5-pyrimidinylboronic acid (17.00 mg, 0.137 mmol) (commercially available from Sigma-Aldrich, Milwaukee, Wis.), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (11.20 mg, 0.014 mmol) (commercially available from Sigma-Aldrich, Milwaukee, Wis.) were combined in dioxane (457 μL) and stirred at 130° C. for 1 hour. LC-MS indicated that there was complete conversion to the desired product. The final reaction mixture was passed through a syringe filter, and the material thus obtained was purified by reverse-phase preparative HPLC using 0.1% TFA in ACN/H2O, gradient 15% to 90% over 20 minutes to provide (S)-5,5-dimethyl-4-phenyl-3-(4-(7-(pyrimidin-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)phenyl)oxazolidin-2-one (15 mg, 0.032 mmol, 23.64% yield) as a tan solid. 1H NMR (400 MHz, DMSO-d6) δ 9.35 (s, 2H), 9.27 (s, 1H), 8.66-8.66 (m, 1H), 8.68 (dd, J=0.88, 6.36 Hz, 1H), 8.45 (dd, J=1.17, 1.86 Hz, 1H), 7.86-7.96 (m, 2H), 7.71-7.81 (m, 2H), 7.51 (dd, J=2.15, 7.43 Hz, 1H), 7.37-7.46 (m, 2H), 7.28-7.37 (m, 3H), 5.57 (s, 1H), 1.67 (s, 3H), 0.94 (s, 3H). m/z (ESI) 463.2 (M+H)+.

Sources & evidence

ORD record
ord-1a646f4b4d8249d7994197a6f9173116
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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