Sodium Carbonate → HCID 19921656, compound

HRID 1463322Notes

Reaction equation

HRID 1463322 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])=[CH:4][C:3]=1I.[Si:15]([O:22][CH2:23][CH2:24][CH2:25][C:26]#[C:27][Si:28]([CH3:31])([CH3:30])[CH3:29])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>CN(C)C=O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Si:15]([O:22][CH2:23][CH2:24][CH2:25][C:26]1[C:3]2[C:2](=[CH:7][CH:6]=[C:5]([CH2:8][S:9]([NH:12][CH3:13])(=[O:11])=[O:10])[CH:4]=2)[NH:1][C:27]=1[Si:28]([CH3:29])([CH3:30])[CH3:31])([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 107584621-(4-Amino-3-iodophenyl)-N-methylmethanesulfonamideHCID 10923628HCID 10923628, compound

Product 1

HCID 19921656HCID 19921656, compoundYield 88%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 0.326 g (1.0 mmol, 1.0 equiv.) of 4-amino-3-iodo-N-methylbenzenemethanesulfonamide in 20 mL of dimethylformamide was added 0.541 g (2.0 mmol, 2.0 equiv.) of 1-t-butyldimethylsilyloxy-5-trimethylsilyl-4-pentyne, 0.278 g (1.0 mmol, 1.0 equiv.) of tetrabutylammonium chloride, 0.530 g (5.0 mmol, 5.0 equiv.) of sodium carbonate, 0.0131 g (0.05 mmol, 0.05 equiv.) of triphenylphosphine, and 0.0112 g (0.05 g, 0.05 equiv.) of palladium (II) acetate. The mixture was heated in a 100° C. oil bath for 16 hours. The mixture was cooled to room temperature and the dimethylformamide removed in vacuo. The residue was diluted with 75 mL of ethyl acetate and washed with 25 mL of saturated aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield an oil. The oil was filtered through a plug of silica gel with 25% ethyl acetate in hexane to yield 0.411 g (88%) of 3-(3-t-butyldimethylsilyloxypropyl)-2-trimethylsilyl-N-methyl-1H-indole-5-methanesulfonamide.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customthe dimethylformamide removed in vacuo
  3. additionThe residue was diluted with 75 mL of ethyl acetate
  4. washwashed with 25 mL of saturated aqueous sodium bicarbonate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto yield an oil
  9. filtrationThe oil was filtered through a plug of silica gel with 25% ethyl acetate in hexane

Sources & evidence

ORD record
ord-83aca1153c294e43bfa371e1651551b0
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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