Potassium trimethylsilanolate → 1-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropane-1-sulfonamide

HRID 558221Notes

Reaction equation

HRID 558221 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]1([S:14]([N:17]2[C:21]3=[N:22][CH:23]4[N:29]([CH3:30])[CH:28]=[N:27][CH:24]4[C:25]([Cl:26])=[C:20]3[N:19]([C:31]3[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=3[F:38])C2=O)(=[O:16])=[O:15])[CH2:13][CH2:12]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C[Si](C)(C)[O-].[K+]>C1COCC1>[Si:1]([O:8][CH2:9][CH2:10][C:11]1([S:14]([NH:17][C:21]2[C:20]([NH:19][C:31]3[CH:36]=[CH:35][C:34]([I:37])=[CH:33][C:32]=3[F:38])=[C:25]([Cl:26])[CH:24]3[N:27]=[CH:28][N:29]([CH3:30])[CH:23]3[N:22]=2)(=[O:16])=[O:15])[CH2:13][CH2:12]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 23668039Potassium trimethylsilanolateHCID 669992833-(1-(2-(Tert-butyldimethylsilyloxy)ethyl)cyclopropylsulfonyl)-8-chloro-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 669994361-(2-(tert-butyldimethylsilyloxy)ethyl)-N-(7-chloro-6-(2-fluoro-4-iodophenylamino)-3-methyl-3a,7a-dihydro-3H-imidazo[4,5-b]pyridin-5-yl)cyclopropane-1-sulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1-(2-(tert-butyldimethylsilyloxy)ethyl)cyclopropylsulfonyl)-8-chloro-1-(2-fluoro-4-iodophenyl)-5-methyl-3,4a,5,7a-tetrahydrodiimidazo[4,5-b:4′,5′-e]pyridin-2(1H)-one (86 mg, 0.124 mmol) in THF (5 ml) is added potassium trimethylsilanolate (80 mg, 0.62 mmol). The resulting solution is stirred at room temperature for 24 h. The reaction is 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 desired product.

Workup

  1. customThe reaction is quenched 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-594c41bd7d15419f8d4c71300bb3b76e
Source dataset
uspto-grants-2011_11
Patent number
US08063049B2

Reaction notes

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