Hydrochloric Acid → HCID 86628683, compound

HRID 2079903Notes

Reaction equation

HRID 2079903 reaction equation
[CH:1]([N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][S:14]([CH3:17])(=[O:16])=[O:15])[CH:11]=2)[C:6]([C:18]2[CH:23]=[CH:22][C:21]([C:24]#[C:25][Si](C)(C)C)=[CH:20][CH:19]=2)=[CH:5]1)([CH3:3])[CH3:2].C(N1C2C(=CC=C(NS(C)(=O)=O)C=2)C(C2C=CC(C#C[Si](C)(C)C)=CN=2)=C1)(C)C.C(=O)([O-])[O-].[K+].[K+].Cl>[Cl-].[Na+].O.O.CO.ClCCl>[C:24]([C:21]1[CH:20]=[CH:19][C:18]([C:6]2[C:7]3[C:12](=[CH:11][C:10]([NH:13][S:14]([CH3:17])(=[O:15])=[O:16])=[CH:9][CH:8]=3)[N:4]([CH:1]([CH3:3])[CH3:2])[CH:5]=2)=[CH:23][CH:22]=1)#[CH:25]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 57442259HCID 57442259, compoundHCID 57442260HCID 57442260, compound

Product 1

HCID 86628683HCID 86628683, compound

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Add N-[1-isopropyl-3-(4-trimethylsilanylethynyl-phenyl)-1H-indol-6-yl]-methanesulfonamide (0.223 mmoles; 95.0 mg, prepared similarly to N-[1-isopropyl-3-(5-trimethylsilanylethynyl-pyridin-2-yl)-1H-indol-6-yl]-methanesulfonamide), dichloromethane (4.0 mL), methanol (4.0 mL); followed by Potassium Carbonate (1.119 mmoles; 154.6 mg) to a round bottom flask equipped with a stir bar. Stir the resulting material for 2 hours at room temperature. Dilute the reaction with water and acidify to pH of 6-7 with 1N HCl. Dilute the resulting aqueous mixture with brine and extract with dichloromethane. Concentrated the resulting mixture in vacuo and then purify the resulting material on a chromatotron (2MM silica gel plate; load CH2Cl2; run 30%-50% ethyl acetate gradient in hexanes) to obtain the desired product as a light-yellow crystalline solid, 50 mg (63%). MS (IS+) m/e 353.0 (M+1)

Workup

  1. customequipped with a stir bar
  2. additionDilute
  3. extractionextract with dichloromethane
  4. concentrationConcentrated the resulting mixture in vacuo
  5. custompurify the resulting material on a chromatotron (2MM silica gel plate; load CH2Cl2; run 30%-50% ethyl acetate gradient in hexanes)

Sources & evidence

ORD record
ord-8ba469db9c6a4df998f1859ec8dc1277
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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