Potassium Iodide → HCID 53492571, compound

HRID 1428976Notes

Reaction equation

HRID 1428976 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([B:27]2[O:31][C:30]([CH3:33])([CH3:32])[C:29]([CH3:35])([CH3:34])[O:28]2)=[CH:23][CH:22]=1.[C:36](#[N:38])C>>[CH3:34][C:29]1([CH3:35])[C:30]([CH3:33])([CH3:32])[O:31][B:27]([C:24]2[CH:25]=[CH:26][C:21]([CH2:20][O:1][C:2]3[CH:10]=[CH:9][C:5]4[N:6]=[C:7]([C:36]#[N:38])[S:8][C:4]=4[CH:3]=3)=[CH:22][CH:23]=2)[O:28]1

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 1518116-HydroxybenzothiazoleHCID 37345062-(4-(Bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Product 1

HCID 53492571HCID 53492571, compoundYield 72%

Procedure

A mixture of 6-hydroxybenzothiazole (0.5 g, 2.84 mmol), potassium carbonate (0.78 g, 5.68 mmol) and potassium iodide (0.94 g, 5.68 mmol) in acetonitrile was heated to reflux for 1 hour. 2-(4-(bromomethyl)phenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.93 g, 3.12 mmol) was added, and the reaction mixture was refluxed overnight. After cooling down, the suspension was extracted with ethyl acetate/water and the residue was purified with flash chromatography to give the product as a white solid (0.8 g, 72%). 1H NMR (300 MHz, CD2Cl2, δ): 8.11 (d, J=9.0 Hz, 1H), 7.81 (d, J=9.0 Hz, 2H), 7.47 (m, 3H), 7.34 (dd, J=9.0 Hz, 1H), 5.22 (s, 2H), 1.35 (s, 9H); MS (ESI) m/z 393.2.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour
  3. temperaturethe reaction mixture was refluxed overnight
  4. temperatureAfter cooling down
  5. extractionthe suspension was extracted with ethyl acetate/water
  6. customthe residue was purified with flash chromatography

Sources & evidence

ORD record
ord-36e148cd65b74654912b7c9640b00681
Source dataset
uspto-grants-2015_01
Patent number
US08937183B2

Reaction notes

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