Pyridine → HCID 57709132, compound

HRID 547032Notes

Reaction equation

HRID 547032 reaction equation
[CH3:1][Si:2]([O:5]S(C(F)(F)F)(=O)=O)([CH3:4])[CH3:3].[CH2:13]([C:15]([C:34]1[CH:39]=[CH:38][C:37]([C:40]#[C:41][C:42]2(O)[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[C:36]([CH3:50])[CH:35]=1)([C:18]1[CH:23]=[CH:22][C:21]([B:24]2[O:28][C:27]([CH3:30])([CH3:29])[C:26]([CH3:32])([CH3:31])[O:25]2)=[C:20]([CH3:33])[CH:19]=1)[CH2:16][CH3:17])[CH3:14].N1C=CC=CC=1.[Cl-].[NH4+]>ClCCl>[CH2:13]([C:15]([C:18]1[CH:23]=[CH:22][C:21]([B:24]2[O:25][C:26]([CH3:32])([CH3:31])[C:27]([CH3:29])([CH3:30])[O:28]2)=[C:20]([CH3:33])[CH:19]=1)([C:34]1[CH:39]=[CH:38][C:37]([C:40]#[C:41][C:42]2([O:5][Si:2]([CH3:4])([CH3:3])[CH3:1])[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44][CH2:43]2)=[C:36]([CH3:50])[CH:35]=1)[CH2:16][CH3:17])[CH3:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 25517Ammonium ChlorideHCID 65367Trimethylsilyl triflateHCID 67065150HCID 67065150, compound

Product 1

HCID 57709132HCID 57709132, compoundYield 30.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoromethanesulfonic acid trimethylsilyl ester (0.37 mL, 2.04 mmol) was added to a solution of the mixture containing 1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenylethynyl)-cycloheptanol (529 mg) and pyridine (0.42 mL, 5.19 mmol) in dichloromethane (4.0 mL) at 0° C., and the mixture was stirred at the same temperature for 90 minutes. An ammonium chloride solution was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 80:20) to give the target compound as a colorless oil (183 mg, 28% in three steps).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. concentrationThe extract was concentrated under reduced pressure
  3. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 80:20)

Sources & evidence

ORD record
ord-63b68025dfac402482e6bd98e8a07fab
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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