Triacetoxyperiodinane → HCID 58268353, compound

HRID 1898291Notes

Reaction equation

HRID 1898291 reaction equation
[C:1]([Si:5]([CH3:44])([CH3:43])[N:6]1[C:10]2=[N:11][CH:12]=[CH:13][C:14]([CH:15]([OH:42])[C:16]3[C:21]([N:22]([CH2:37][O:38][CH3:39])[S:23]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:35])[F:34])[CH:27]=4)(=[O:25])=[O:24])=[CH:20][C:19]([Cl:40])=[C:18]([CH3:41])[N:17]=3)=[C:9]2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[C:1]([Si:5]([CH3:44])([CH3:43])[N:6]1[C:10]2[N:11]=[CH:12][CH:13]=[C:14]([C:15]([C:16]3[C:21]([N:22]([CH2:37][O:38][CH3:39])[S:23]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[C:28]([C:33]([F:36])([F:34])[F:35])[CH:27]=4)(=[O:25])=[O:24])=[CH:20][C:19]([Cl:40])=[C:18]([CH3:41])[N:17]=3)=[O:42])[C:9]=2[CH:8]=[CH:7]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 58268249HCID 58268249, compound

Product 1

HCID 58268353HCID 58268353, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(2-{[1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-hydroxy-methyl}-5-chloro-6-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethylbenzenesulfonamide (from above step), Dess-Martin periodinane (424 mg, 1.0 mmol) in 3 ml of DCM was stirred at room temperature for overnight. The mixture was directly purified by flash chromatography (25% ethyl acetate in hexane) to afford the desired title compound. MS (ES) (M++H) expect 687. found 686.9

Workup

  1. customThe mixture was directly purified by flash chromatography (25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-16210530c99f4828bc4f006e6f67f12d
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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