Sodium Iodide → HCID 58052428, compound

HRID 2190191Notes

Reaction equation

HRID 2190191 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])=[C:11]([CH:14]3[CH2:16][CH2:15]3)[CH:12]=2)[O:7][C:6]=1[C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=1)=[O:4].[Na+].[I-].C([O-])([O-])=O.[Cs+].[Cs+]>CC(N(C)C)=O.CCOC(C)=O>[CH3:1][NH:2][C:3]([C:5]1[C:13]2[C:8](=[N:9][C:10]([N:17]([CH2:22][CH2:6][CH:5]=[CH2:3])[S:18]([CH3:21])(=[O:20])=[O:19])=[C:11]([CH:14]3[CH2:15][CH2:16]3)[CH:12]=2)[O:7][C:6]=1[C:22]1[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1)=[O:4]

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 58052402HCID 58052402, compound

Product 1

HCID 58052428HCID 58052428, compoundYield 148.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-cyclopropyl-6-methanesulfonylamino-2-p-tolyl-furo[2,3-b]pyridine-3-carboxylic acid methylamide (900 mg, 2.25 mmol, 1.0 equiv) in DMA (2.0 mL) was added NaI (169 mg, 1.12 mmol, 0.5 equiv) and Cs2CO3 (2.2 g, 6.76 mmol, 3.0 equiv) and the resulting mixture was heated at 110° C. for 1 hour. The mixture was then diluted with EtOAc and washed with water, brine, dried over MgSO4 and concentrated. The residue wad purified by silica gel column chromatography, EtOAc/heptane (70%) to give product 760 mg. MS (ESI) m/z 454.5 (M+1). Retention time=1.58 min, Method LC-C8 broad range-NpH.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customThe residue wad purified by silica gel column chromatography, EtOAc/heptane (70%)

Sources & evidence

ORD record
ord-fa20fbcbad494d088fcef1c7750cc7fd
Source dataset
uspto-grants-2012_12
Patent number
US08324239B2

Reaction notes

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