Triacetoxyperiodinane → 2-(4-Chloro-phenyl)-5-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-one

HRID 601528Notes

Reaction equation

HRID 601528 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:20][C:21]([C:23]2[S:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH2:35][CH2:36]O)=[O:22])[CH:6]=[CH:7][C:8]=1[O:9][Si:10]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:13])[CH3:12].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.[OH-].[Na+]>[Cl:34][C:31]1[CH:30]=[CH:29][C:28]([C:26]2[S:27][C:23]3[C:21](=[O:22])[N:20]([C:5]4[CH:6]=[CH:7][C:8]([O:9][Si:10]([CH:11]([CH3:12])[CH3:13])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:15])[CH3:16])=[C:3]([O:2][CH3:1])[CH:4]=4)[CH:36]=[CH:35][C:24]=3[N:25]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 575017112-(4-Chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid (3-methoxy-4-triisopropylsilanyloxy-phenyl)-amide

Product 1

HCID 575017642-(4-Chloro-phenyl)-5-(3-methoxy-4-triisopropylsilanyloxy-phenyl)-5H-thiazolo[5,4-c]pyridin-4-oneYield 48.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Treat a solution 2-(4-chloro-phenyl)-4-(2-hydroxy-ethyl)-thiazole-5-carboxylic acid (3-methoxy-4-triisopropylsilanyloxy-phenyl)-amide (1.0 g, 1.79 mmol) in CH2Cl2 (30 mL) with Dess-Martin periodinane (1.13 g, 2.67 mmol). Stir at room temperature for 18 h, dilute with 1N NaOH, and extract with CH2Cl2 (2×). Dry, filter, and concentrate the organic solution and purify the crude material by flash chromatography, using a gradient of 0-10% MeOH in CH2Cl2 to give the title compound (0.47 g, 48%). MS (ES+) 541.0 (M+1)+. 1H NMR (400 MHz, CDCl3) δ: 8.01 (d, 2H, J=8.8 Hz), 7.46 (d, 2H, J=8.4 Hz), 7.41 (d, 1H, J=7.5 Hz), 6.93 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.80 (s, 3H), 1.25 (m, 3H), 1.09 (d, 18H, J=7.5 Hz).

Workup

  1. extractionextract with CH2Cl2 (2×)
  2. customDry
  3. filtrationfilter
  4. concentrationconcentrate the organic solution
  5. custompurify the crude material by flash chromatography

Sources & evidence

ORD record
ord-33957ed78af54d7ca5ee7c3703bc08a1
Source dataset
uspto-grants-2011_03
Patent number
US07902356B2

Reaction notes

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