Triacetoxyperiodinane → HCID 86645708, compound

HRID 389068Notes

Reaction equation

HRID 389068 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[S:36][C:35]([CH2:37][OH:38])=[N:34][C:29]=3[CH:30]=[N:31][C:32]=2[CH:33]=1>ClCCl>[Br:23][C:24]1[CH:25]=[CH:26][C:27]2[C:28]3[S:36][C:35]([CH:37]=[O:38])=[N:34][C:29]=3[CH:30]=[N:31][C:32]=2[CH:33]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 67542817HCID 67542817, compound

Product 1

HCID 86645708HCID 86645708, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin periodinane (2.16 g, 5.08 mol, [1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3-(1H)-one]) was added to a suspension of (7-bromo[1,3]thiazolo[4,5-c]quinolin-2-yl)methanol (prepared in Part F of Example 2, 1.0 g, 3.4 mmol) in dichloromethane (30 mL), and the resulting suspension was stirred at room temperature for 1.5 hours. The reaction mixture was filtered to isolate solid, which was washed with dichloromethane and diethyl ether to provide 877 mg of 7-bromo[1,3]thiazolo[4,5-c]quinoline-2-carbaldehyde as a brown solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customto isolate solid, which
  3. washwas washed with dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-f84f0988ac23404582d1a61a21f4aae9
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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