Trimethylsilyl iodide → HCID 86760980, compound

HRID 1432953Notes

Reaction equation

HRID 1432953 reaction equation
[Si](I)(C)(C)C.C(OC([N:16]1[CH2:21][CH2:20][N:19]([CH2:22][C:23]2[N:31]([S:32]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)(=[O:34])=[O:33])[C:30]3[CH:29]=[CH:28][N:27]=[C:26]([Cl:41])[C:25]=3[CH:24]=2)[C:18](=[O:42])[CH2:17]1)=O)C1C=CC=CC=1>CC#N>[C:35]1([S:32]([N:31]2[C:30]3[CH:29]=[CH:28][N:27]=[C:26]([Cl:41])[C:25]=3[CH:24]=[C:23]2[CH2:22][N:19]2[CH2:20][CH2:21][NH:16][CH2:17][C:18]2=[O:42])(=[O:33])=[O:34])[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 86760979HCID 86760979, compound

Product 1

HCID 86760980HCID 86760980, compoundYield 18.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

TMSI (2.7 mL, 19.0 mmol) is added to a solution of 4-(1-benzenesulfonyl-4-chloro-1H-pyrrolo[3,2-c]pyridin-2-ylmethyl)-3-oxo-piperazine-1-carboxylic acid benzyl ester (5.06 g, 9.38 mmol) in CH3CN (134 mL) at 0° C. The reaction mixture is warmed to RT and stirred for 5 hours. The reaction mixture is concentrated to dryness and the red residue is diluted with MeOH and concentrated to dryness (this is repeated twice). The mixture is diluted with CH2Cl2 and washed with saturated NaHCO3 and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness. The crude product is chromatographed eluting with 1-5% MeOH/CH2Cl2 to yield the title product (0.70 g, 1.74 mmol) and unreacted starting material (3.58 g, 6.64 mmol). 1H NMR (CDCl3, 300 MHz) δ8.20 (d, 1H), 7.93 (d, 1H), 7.85 (d, 2H), 7.60 (d, 1H), 7.51 (m, 2H), 6.50 (s, 1H), 5.01 (s, 2H), 3.45 (m, 2H), 3.18 (m, 2H). Ion spray [M+H]+=405, 407, Cl pattern.

Workup

  1. concentrationThe reaction mixture is concentrated to dryness
  2. additionthe red residue is diluted with MeOH
  3. concentrationconcentrated to dryness (this is repeated twice)
  4. additionThe mixture is diluted with CH2Cl2
  5. washwashed with saturated NaHCO3 and brine
  6. dry with materialThe organic layer is dried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product is chromatographed
  10. washeluting with 1-5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-1aefe23132a6423eaf8495903b038abd
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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