Ammonium Chloride → [5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl Ester

HRID 546975Notes

Reaction equation

HRID 546975 reaction equation
[CH2:1]([C:3]([C:25]1[CH:30]=[CH:29][C:28](B2OC(C)(C)C(C)(C)O2)=[C:27]([CH3:40])[CH:26]=1)([C:6]1[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]2([O:19][Si:20]([CH3:23])([CH3:22])[CH3:21])[CH2:18][CH2:17][CH2:16][CH2:15]2)=[C:8]([CH3:24])[CH:7]=1)[CH2:4][CH3:5])[CH3:2].[CH3:41][O:42][C:43](=[O:52])[CH2:44][C:45]1[CH:50]=[CH:49][C:48](Br)=[CH:47][N:46]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>CN(C)C=O>[CH3:41][O:42][C:43](=[O:52])[CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:28]2[CH:29]=[CH:30][C:25]([C:3]([CH2:1][CH3:2])([C:6]3[CH:11]=[CH:10][C:9]([C:12]#[C:13][C:14]4([O:19][Si:20]([CH3:22])([CH3:21])[CH3:23])[CH2:18][CH2:17][CH2:16][CH2:15]4)=[C:8]([CH3:24])[CH:7]=3)[CH2:4][CH3:5])=[CH:26][C:27]=2[CH3:40])=[CH:47][N:46]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 53419526Methyl 2-(5-broMopyridin-2-yl)acetateHCID 577089762-(4-{1-Ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane

Product 1

HCID 57709210[5-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-pyridin-2-yl]-acetic Acid Methyl EsterYield 31.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2-(4-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-2-methyl-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Example 32-(4); 60.8 mg, 0.10 mmol), (5-bromo-pyridin-2-yl)acetic acid methyl ester (Example 44-(2); 43.5 mg, 0.18 mmol), tetrakistriphenylphosphine palladium (17.3 mg, 0.015 mmol) and potassium phosphate (34.1 mg, 0.16 mmol) in N,N-dimethylformamide (0.6 mL) was stirred at 85° C. for four hours. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 60% ethyl acetate/hexane) to give the title compound (18.1 mg, 28%).

Workup

  1. customwas stirred at 85° C. for four hours
  2. extractionfollowed by extraction with diethyl ether
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (20% ethyl acetate/hexane to 60% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6ce0e4340c524ad6a95ea5ddda75e2a0
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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