Potassium Phosphate, Tribasic → (E)-[5-(4-{1-ethyl-1-[4-(3-ethyl-3-hydroxy-1-pentenyl)-3-methyl-phenyl]-propyl}-phenyl)-pyridin-3-yl]-acetic Acid Methyl Ester

HRID 547017Notes

Reaction equation

[CH2:1]([C:3]([OH:35])([CH2:33][CH3:34])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH2:30][CH3:31])([C:15]2[CH:20]=[CH:19][C:18](B3OC(C)(C)C(C)(C)O3)=[CH:17][CH:16]=2)[CH2:13][CH3:14])=[CH:8][C:7]=1[CH3:32])[CH3:2].[CH3:36][O:37][C:38](=[O:47])[CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[C:44](Br)[CH:45]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C)C=O>[CH3:36][O:37][C:38](=[O:47])[CH2:39][C:40]1[CH:41]=[N:42][CH:43]=[C:44]([C:18]2[CH:17]=[CH:16][C:15]([C:12]([CH2:30][CH3:31])([C:9]3[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([CH2:33][CH3:34])([OH:35])[CH2:1][CH3:2])=[C:7]([CH3:32])[CH:8]=3)[CH2:13][CH3:14])=[CH:20][CH:19]=2)[CH:45]=1

Participants

Conditions

Temperature: 140 °C

Procedure

A solution of (E)-3-ethyl-1-(4-{1-ethyl-1-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-penten-3-ol (Example 39-(5); 50.0 mg, 0.10 mmol), (5-bromo-pyridin-3-yl)acetic acid methyl ester (Example 24-(2); 36.2 mg, 0.15 mmol), tetrakistriphenylphosphine palladium (16.8 mg, 0.0146 mmol) and potassium phosphate (33.4 mg, 0.15 mmol) in N,N-dimethylformamide (0.30 mL) was stirred with microwave heating at 140° C. for 10 minutes. The reaction mixture was filtered through cotton plug, and the residue was purified by silica gel chromatography (40 to 50% ethyl acetate/hexane) to give the title compound (46.5 mg, 88%).

Workup

filtrationThe reaction mixture was filtered through cotton plug
customthe residue was purified by silica gel chromatography (40 to 50% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-bcb90ed03fe44da684042bab1d412d04
Source dataset: uspto-grants-2011_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07935688B2

Reaction notes

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