Ammonium Chloride → HCID 57708963, compound

HRID 547111Notes

Reaction equation

HRID 547111 reaction equation
[C:1]([Si:5]([O:8][CH:9]([CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]([CH2:41][CH3:42])([C:25]2[CH:30]=[CH:29][C:28](B3OC(C)(C)C(C)(C)O3)=[C:27]([CH3:40])[CH:26]=2)[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:43])[C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[CH3:44][O:45][C:46](=[O:80])[CH2:47][C:48]1[CH:53]=[C:52]([O:54]S(C(F)(F)F)(=O)=O)[CH:51]=[C:50](O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH:49]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[Cl-].[NH4+]>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>[CH3:44][O:45][C:46](=[O:80])[CH2:47][C:48]1[CH:49]=[C:50]([C:28]2[CH:29]=[CH:30][C:25]([C:22]([C:19]3[CH:20]=[CH:21][C:16]([CH2:15][CH2:14][CH:9]([O:8][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:6])[CH3:7])[C:10]([CH3:13])([CH3:12])[CH3:11])=[C:17]([CH3:43])[CH:18]=3)([CH2:23][CH3:24])[CH2:41][CH3:42])=[CH:26][C:27]=2[CH3:40])[CH:51]=[C:52]([OH:54])[CH:53]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 577089262-[4-(1-{4-[3-(t-Butyldimethyl-silanyloxy)-4,4-dimethyl-pentyl]-3-methyl-phenyl}-1-ethyl-propyl)-2-methyl-phenyl]-4,4,5,5-tetramethyl-[1,3,2]dioxaborolaneHCID 57708958HCID 57708958, compound

Product 1

HCID 57708963HCID 57708963, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
85 °C

Procedure

Degassed N,N-dimethylformamide (0.24 mL) was added to t-butyl-(1-{2-[4-(1-ethyl-1-{4-[4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl]-3-methyl-phenyl}-propyl)-2-methyl-phenyl]-ethyl}-2,2-dimethyl-propoxy)dimethylsilane (Example 24-(1); 17.4 mg, 0.0287 mmol), [3-(t-butyl-diphenyl-silanyloxy)-5-trifluoromethanesulfonyloxy-phenyl]acetic acid methyl ester (Example 164-(2); 17.1 mg, 0.0309 mmol), tetrakis(triphenylphosphine)palladium (0) (5.4 mg, 0.0047 mmol) and potassium phosphate (11.5 mg, 0.0542 mmol). After replacement with nitrogen, the mixture was heated while stirring at an external temperature of 80 to 90° C. for 15 hours. 50% saturated aqueous ammonium chloride was added to the reaction mixture, followed by extraction with diethyl ether. The extract was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1) to give the title compound (15.9 mg, 86%).

Workup

  1. customDegassed N,N-dimethylformamide (0.24 mL)
  2. temperatureAfter replacement with nitrogen, the mixture was heated
  3. extractionfollowed by extraction with diethyl ether
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane/ethyl acetate=5/1)

Sources & evidence

ORD record
ord-f18d501d71c846c2be12d4bb82235d55
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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