Trimethylsilyl iodide → HCID 21182795, compound

HRID 1387117Notes

Reaction equation

HRID 1387117 reaction equation
CO[C:3]([N:5](C)[C:6]1[CH:7]=[C:8]([C:18]([C:20]2[C:21]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:39][C:22]=3[S:23][C:24]=2[C:25]2[CH:30]=[CH:29][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:27][CH:26]=2)=[O:19])[CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)=O.C[Si](I)(C)C>C(Cl)Cl>[CH3:3][NH:5][C:6]1[CH:7]=[C:8]([C:18]([C:20]2[C:21]3[CH:42]=[CH:41][C:40]([O:43][CH2:44][C:45]4[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=4)=[CH:39][C:22]=3[S:23][C:24]=2[C:25]2[CH:26]=[CH:27][C:28]([O:31][CH2:32][CH2:33][N:34]3[CH2:38][CH2:37][CH2:36][CH2:35]3)=[CH:29][CH:30]=2)=[O:19])[CH:9]=[CH:10][C:11]=1[CH2:12][N:13]1[CH2:14][CH2:15][CH2:16][CH2:17]1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 21182999HCID 21182999, compound

Product 1

HCID 21182795HCID 21182795, compoundYield 37.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The 379 mg of 6-benzyloxy-2-[4-[2-(1-pyrrolidinyl)ethoxy]phenyl]benzo[b]thiophen-3-yl 3-[(methoxycarbonyl)(methyl)amino]-4-(1-pyrrolidinylmethyl)phenyl ketone (Part G) was dissolved in 5.5 mL of dry CH2Cl2. To the solution was added 0.31 mL of trimethylsilyl iodide. The reaction mixture was stirred for 5.5 h. The reaction was quenched with 0.3 mL of MeOH and the mixture was concentrated to dryness under reduced pressure. Purification by flash chromatography (silica gel, 5% to 8% [10% conc NH4OH/MeOH]/CH2Cl2) afforded 130 mg (0.201 mmol, 37%) of a yellow foam.

Workup

  1. customThe reaction was quenched with 0.3 mL of MeOH
  2. concentrationthe mixture was concentrated to dryness under reduced pressure
  3. customPurification by flash chromatography (silica gel, 5% to 8% [10% conc NH4OH/MeOH]/CH2Cl2)

Sources & evidence

ORD record
ord-394de76fe0b3469c8ca834688fc81b83
Source dataset
uspto-grants-2001_07
Patent number
US06265575B1

Reaction notes

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