Pyridine → HCID 57709043, compound

HRID 547021Notes

Reaction equation

HRID 547021 reaction equation
N1C=CC=CC=1.[O:7]([Si:15]([CH3:18])([CH3:17])[CH3:16])S(C(F)(F)F)(=O)=O.[CH2:19]([C:21](O)([CH2:52][CH3:53])[C:22]#[C:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([CH2:49][CH3:50])([C:33]2[CH:38]=[CH:37][C:36]([B:39]3[O:43][C:42]([CH3:45])([CH3:44])[C:41]([CH3:47])([CH3:46])[O:40]3)=[C:35]([CH3:48])[CH:34]=2)[CH2:31][CH3:32])=[CH:26][C:25]=1[CH3:51])[CH3:20].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:31]([C:30]([C:33]1[CH:38]=[CH:37][C:36]([B:39]2[O:40][C:41]([CH3:46])([CH3:47])[C:42]([CH3:45])([CH3:44])[O:43]2)=[C:35]([CH3:48])[CH:34]=1)([C:27]1[CH:28]=[CH:29][C:24]([C:23]#[C:22][C:21]([CH2:19][CH3:20])([O:7][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH2:52][CH3:53])=[C:25]([CH3:51])[CH:26]=1)[CH2:49][CH3:50])[CH3:32]

Participants

6

Reactant 4

HCID 1049PyridineHCID 65367Trimethylsilyl triflateHCID 516892Sodium BicarbonateHCID 57708970HCID 57708970, compound

Product 1

HCID 57709043HCID 57709043, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (0.116 mL, 1.432 mmol) and trimethylsilyl triflate (0.129 mL, 0.716 mmol) were added to a solution of 3-ethyl-1-(4-{1-ethyl-1-[3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-propyl}-2-methyl-phenyl)-1-pentyn-3-ol (Example 125-(2); 175 mg, 0.358 mmol) in dichloromethane (5 mL) at 0° C., and the mixture was stirred for one hour. The reaction mixture was then poured into a saturated aqueous sodium bicarbonate solution, followed by extraction with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30) to give the target compound as a colorless oil (158 mg, 79%).

Workup

  1. extractionfollowed by extraction with dichloromethane
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by silica gel chromatography (hexane:ethyl acetate=100:0 to 70:30)

Sources & evidence

ORD record
ord-06daaf1ec2b74207bc19b01ece202607
Source dataset
uspto-grants-2011_05
Patent number
US07935688B2

Reaction notes

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