Acetonitrile → HCID 67043662, compound

HRID 1503463Notes

Reaction equation

HRID 1503463 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][C:6]1([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]1)[C:5]2=[N:18][S:19]([CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])(=[O:21])=[O:20].[C:28]([O-:31])([O-])=O.[K+].[K+].Br[CH2:35][CH2:36]C(F)(F)F.[CH3:41]C#N>>[Br:1][C:2]1[CH:3]=[C:4]2[C:8]([CH2:7][C:6]3([CH2:15][CH2:14][CH:13]([O:16][CH3:17])[CH2:12][CH2:11]3)[C:5]2([NH:18][S:19]([CH2:22][CH2:23][Si:24]([CH3:26])([CH3:25])[CH3:27])(=[O:21])=[O:20])[C:35]([O:31][CH2:28][CH3:41])=[CH2:36])=[CH:9][CH:10]=1

Participants

5

Reactant 4

HCID 6342Acetonitrile2×HCID 11430Potassium CarbonateHCID 27251143-Bromo-1,1,1-trifluoropropaneHCID 67043529N-(5'-bromo-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-(trimethylsilyl)ethanesulfonamide

Product 1

HCID 67043662HCID 67043662, compoundYield 80%

Procedure

To a solution of compound 8 (100 mg, 0.27 mmol) in CH3CN (5 mL) was added K2CO3 (74 mg, 0.54 mmol). After addition, the resulting mixture was stirred at room temperature for 10 min. Then 3-bromo-1,1,1-trifluoro-propane (47.8 mg, 0.27 mmol) in CH3CN (5 mL) was added dropwise via a syringe with stirring. The mixture was stirred at 60° C. overnight, and then the mixture was filtered off, the filtrate was concentrated to give compound 9 (97 mg, 80%) as a white solid, which was used for the next step directly without purification. LC-MS tR=1.392 min in 2 min chromatography, MS (ESI) m/z 467.2 [M+H]+.

Workup

  1. additionAfter addition
  2. stirringwith stirring
  3. stirringThe mixture was stirred at 60° C. overnight
  4. filtrationthe mixture was filtered off
  5. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-72b45fa37cef4e4f9d5e01cae519fc9a
Source dataset
uspto-grants-2015_12
Patent number
US09212153B2

Reaction notes

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