Sodium Thiosulfate → HCID 58268180, compound

HRID 1898283Notes

Reaction equation

HRID 1898283 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[CH:22]([OH:39])[C:23]2[CH:28]=[CH:27][N:26]=[C:25]3[N:29]([Si:32]([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33])[CH:30]=[CH:31][C:24]=23)[CH2:12][O:13][CH3:14])(=[O:10])=[O:9])=[CH:4][C:3]=1[C:40]([F:43])([F:42])[F:41].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C:15]2[CH:20]=[C:19]([Cl:21])[CH:18]=[CH:17][C:16]=2[C:22]([C:23]2[C:24]3[CH:31]=[CH:30][N:29]([Si:32]([C:35]([CH3:37])([CH3:38])[CH3:36])([CH3:33])[CH3:34])[C:25]=3[N:26]=[CH:27][CH:28]=2)=[O:39])[CH2:12][O:13][CH3:14])(=[O:9])=[O:10])=[CH:4][C:3]=1[C:40]([F:43])([F:42])[F:41]

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 58268098HCID 58268098, compound

Product 1

HCID 58268180HCID 58268180, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-chloro-N-{5-chloro-2-[hydroxy-(1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridin-4-yl)-methyl]-phenyl}-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (88 mg, 0.13 mmol) in CH2Cl2 (3 mL) was added Dess-Martin periodinane (99.8 mg, 0.235 mmol) and stirred for 5 h at room temperature. 10% Na2S2O3 (3 mL) and saturated aqueous NaHCO3 solution (3 mL) was added and stirred for 30 min. Aqueous layer was separated and extracted with EtOAc (2×25 mL). Combined organic layers were washed with saturated aqueous NaHCO3 solution (20 mL), brine (20 mL), dried (anhydrous Na2SO4), concentrated and column purified (SiO2, 30% EtOAc-hexanes) to obtain 4-chloro-N-[5-chloro-2-(1-(tert-butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbonyl)-phenyl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (80 mg) in 92% yield. ESMS m/z (relative intensity): 672 (M+H)+ (100).

Workup

  1. stirringstirred for 30 min
  2. customAqueous layer was separated
  3. extractionextracted with EtOAc (2×25 mL)
  4. washCombined organic layers were washed with saturated aqueous NaHCO3 solution (20 mL), brine (20 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. concentrationconcentrated
  7. customcolumn purified (SiO2, 30% EtOAc-hexanes)

Sources & evidence

ORD record
ord-7d727a00461a43508b471a9c9bac12d7
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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