Pyridine → HCID 58026145, compound

HRID 2387313Notes

Reaction equation

HRID 2387313 reaction equation
[CH3:1][C:2]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20](O)=[O:21])([CH3:17])[CH2:3][C:4]([C:13]([F:16])([F:15])[F:14])([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C:6]#[CH:7].[N:27]1C=CC=CC=1.S(Cl)(Cl)=O>ClCCl>[CH3:1][C:2]([C:18]1[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=1[C:20]([NH2:27])=[O:21])([CH3:17])[CH2:3][C:4]([C:13]([F:16])([F:15])[F:14])([O:8][Si:9]([CH3:12])([CH3:11])[CH3:10])[CH2:5][C:6]#[CH:7]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 580261432-(1,1-Dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzoic acid

Product 1

HCID 58026145HCID 58026145, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(1,1-dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzoic acid (246 mg, 0.64 mmol) in 5 mL of dichloromethane was added pyridine (77 μL, 0.96 mmol) followed by thionyl chloride (56 μL, 0.76 mmol). The reaction was stirred for 15 minutes then the volatiles were removed in vacuo. The crude acid chloride was treated with 7 M ammonia in 5.0 mL of MeOH. The mixture was stirred for 15 minutes then diluted with 75 mL of EtOAc, washed with two 25 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification of the crude by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc) gave 2-(1,1-dimethyl-3-trifluoromethyl-3-trimethylsilanyloxyhex-5-ynyl)benzamide as a pale yellow solid (108 mg, 44%). MS (ES+) m/z 386 [M+H]+.

Workup

  1. customthe volatiles were removed in vacuo
  2. additionThe crude acid chloride was treated with 7 M ammonia in 5.0 mL of MeOH
  3. stirringThe mixture was stirred for 15 minutes
  4. additionthen diluted with 75 mL of EtOAc
  5. washwashed with two 25 mL portions of saturated aqueous sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification of the crude by flash chromatography (12 g SiO2, hexanes to 1:1 hexanes:EtOAc)

Sources & evidence

ORD record
ord-fac19b4586474ebabb2743b107f4b43d
Source dataset
uspto-grants-2012_09
Patent number
US08268859B2

Reaction notes

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