Potassium Iodide → tert-Butyl {2-[3-(2,3-dihydro-1-ethyloxycarbonyl-3-oxo-indazol-2-yl)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

HRID 2389477Notes

Reaction equation

HRID 2389477 reaction equation
[SH:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1.[CH2:19]([O:21][C:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[CH2:34][CH2:35][CH2:36]Cl)=[O:23])[CH3:20].[I-].[K+].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:19]([O:21][C:22]([N:24]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26](=[O:33])[N:25]1[CH2:34][CH2:35][CH2:36][S:1][C:2]1[N:6]([CH2:7][C:8]([O:10][C:11]([CH3:13])([CH3:14])[CH3:12])=[O:9])[C:5]2[CH:15]=[CH:16][CH:17]=[CH:18][C:4]=2[N:3]=1)=[O:23])[CH3:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 693147462-(3-Chloro-propyl)-3-oxo-2,3-dihydro-indazole-1-carboxylic acid ethyl esterHCID 178451223HCID 178451223, compound

Product 1

HCID 86620027tert-Butyl {2-[3-(2,3-dihydro-1-ethyloxycarbonyl-3-oxo-indazol-2-yl)-propylsulfanyl]-benzoimidazol-1-yl}-acetate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of tert-butyl (2-mercapto-benzoimidazol-1-yl)-acetate (Intermediate 3-I, 66 mg, 0.25 mmol), 2-(3-chloro-propyl)-3-oxo-2,3-dihydro-indazole-1-carboxylic acid ethyl ester (alkylating agent G-01d, 70 mg, 0.25 mmol), a few crystals of potassium iodide and K2CO3 (69 mg, 0.5 mmol) in acetone (1 ml) is refluxed overnight. Evaporation of the solvent under a stream of air affords a residue that is purified by flash-chromatography on silica-gel (AcOEt/heptane, 3:2), yielding the title compound as a colourless oil: tR=2.75 min (LC-2), ESI-MS (pos.): m/z 511.15 [M+H]+; 1H-NMR (CDCl3): δ (ppm) 1.37 (s, 9H, tBu), 1.37 (t, 3H, CH3), 2.14 (quint., 2H, CH2CH2N), 3.28 (m, 2H, SCH2), 4.30-4.40 (m, 4H), 4.69 (s, 2H, CH2CO2), 7.10 (m, 3Harom), 7.26 (t, 1Harom), 7.55 (m, 2Harom), 7.81 (t, 2Harom).

Workup

  1. customEvaporation of the solvent under a stream of air
  2. customaffords a residue that
  3. customis purified by flash-chromatography on silica-gel (AcOEt/heptane, 3:2)

Sources & evidence

ORD record
ord-8c7af3d463dc427fae97448ada1b2238
Source dataset
uspto-grants-2012_09
Patent number
US08273740B2

Reaction notes

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