Potassium trimethylsilanolate → N-(7-Chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropanesulfonamide

HRID 558219Notes

Reaction equation

HRID 558219 reaction equation
[Cl:1][C:2]1[CH:7]2[N:8]=[CH:9][N:10]([CH3:11])[CH:6]2[N:5]=[C:4]2[N:12]([S:24]([CH:27]3[CH2:29][CH2:28]3)(=[O:26])=[O:25])C(=O)[N:14]([C:15]3[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=3[F:22])[C:3]=12.C[Si](C)(C)[O-].[K+]>C1COCC1>[Cl:1][C:2]1[CH:7]2[N:8]=[CH:9][N:10]([CH3:11])[CH:6]2[N:5]=[C:4]([NH:12][S:24]([CH:27]2[CH2:29][CH2:28]2)(=[O:26])=[O:25])[C:3]=1[NH:14][C:15]1[CH:20]=[CH:19][C:18]([I:21])=[CH:17][C:16]=1[F:22]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 669992718-Chloro-3-(cyclopropylsulfonyl)-1-(2-fluoro-4-iodophenyl)-5-methyl-3,4a,5,7a-tetrahydrodiimidazo[4,5-b:4',5'-e]pyridin-2(1H)-one

Product 1

HCID 66998952N-(7-Chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 8-chloro-3-(cyclopropylsulfonyl)-1-(2-fluoro-4-iodophenyl)-5-methyl-3,4a,5,7a-tetrahydrodiimidazo[4,5-b:4′,5′-e]pyridin-2(1H)-one (79 mg, 0.144 mmol) in THF (5 ml) is added potassium trimethylsilanolate (55 mg, 0.43 mmol). The reaction is stirred at room temperature for 16 h, quenched with saturated aqueous NH4Cl solution (10 ml) and extracted with EtOAc (2×10 ml). The combined organic solution is washed with brine (10 ml), dried over MgSO4 and concentrated. Silica gel chromatography yields the title compound.

Workup

  1. customquenched with saturated aqueous NH4Cl solution (10 ml)
  2. extractionextracted with EtOAc (2×10 ml)
  3. washThe combined organic solution is washed with brine (10 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-7da0707a7e584c77885b66d704e6a1cd
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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