Triacetoxyperiodinane → HCID 86634725, compound

HRID 910959Notes

Reaction equation

HRID 910959 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][C:24]1[N:25]=[C:26]([NH:29][C:30]2[N:35]=[CH:34][C:33]([CH2:36][OH:37])=[C:32]([O:38][C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=[CH:41][CH:40]=3)[CH:31]=2)[S:27][CH:28]=1>C1COCC1.CCOCC.[OH-].[Na+]>[CH3:23][C:24]1[N:25]=[C:26]([NH:29][C:30]2[CH:31]=[C:32]([O:38][C:39]3[C:48]4[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=4)[CH:42]=[CH:41][CH:40]=3)[C:33]([CH:36]=[O:37])=[CH:34][N:35]=2)[S:27][CH:28]=1

Participants

6

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 24826338HCID 24826338, compound

Product 1

HCID 86634725HCID 86634725, compoundYield 93.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of Dess Martin periodane (1.30 g, 3.05 mmol) in THF (5 mL) at 0° C. was added a solution of (6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)pyridin-3-yl)methanol (0.925 g, 2.55 mmol). The mixture was warmed to room temperature and stirred for 30 minutes, diluted with ether and hydrolyzed with 1N NaOH (40 mL). The mixture was extracted with ether, washed with brine, dried, and concentrated to afford 6-(4-methylthiazol-2-ylamino)-4-(naphthalen-1-yloxy)nicotinaldehyde (0.860 g, 93.5% yield) as a light yellow solid. 1H NMR (DMSO d6) δ 11.28 (bs, 1H), 10.40 (s, 1H), 8.75 (s, 1H), 8.09 (d, 1H), 7.98 (d, 1H), 7.92 (d, 1H), 7.55-7.68 (m, 3H), 7.49 (d, 1H), 6.62 (s, 1H), 6.26 (bs, 1H), 2.13 (s, 3H).

Workup

  1. extractionThe mixture was extracted with ether
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-394b506e41064e3cb08197f4f7776539
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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