4-Toluenesulfonyl chloride → N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide

HRID 2240248Notes

Reaction equation

HRID 2240248 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:22])[F:21])=[CH:14][C:13]=2[F:25])[NH:4][CH:3]=1.C([Li])CCC.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37](Cl)(=[O:39])=[O:38])=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>C1COCC1.O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[CH:8][C:9]=2[CH2:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:24])[C:20]([F:23])([F:21])[F:22])=[CH:14][C:13]=2[F:25])[N:4]([S:37]([C:34]2[CH:35]=[CH:36][C:31]([CH3:41])=[CH:32][CH:33]=2)(=[O:39])=[O:38])[CH:3]=1

Participants

7

Reactant 4

HCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 59305008N-{4-[(3-Bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamideHCID 178418339Butyllithium

Product 1

HCID 59304989N-[4-({3-Bromo-1-[(4-methylphenyl)sulfonyl]-1H-pyrrolo[2,3-b]pyridin-4-yl}methyl)-3-fluorophenyl]-2,2,2-trifluoroacetamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

1.70 g (4.08 mmol) of N-{4-[(3-bromo-1H-pyrrolo[2,3-b]pyridin-4-yl)methyl]-3-fluorophenyl}-2,2,2-trifluoroacetamide are dissolved in 50 ml of THF and cooled to −78° C. A solution of n-butyllithium (2.81 ml, 1.6M in hexane, 4.49 mmol) is added dropwise. After 15 min, a solution of 860 mg (4.49 mmol) of p-toluenesulfonyl chloride in 5 ml of THF is added dropwise. The mixture is allowed to warm to RT and stirred for 1 h. Water and saturated sodium bicarbonate solution are then added, and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulfate. The solvent is removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase dichloromethane:ethanol=50:1).

Workup

  1. temperatureto warm to RT
  2. extractionthe mixture is extracted with ethyl acetate
  3. dry with materialThe organic phase is dried over sodium sulfate
  4. customThe solvent is removed under reduced pressure
  5. customthe residue is purified by column chromatography on silica gel (mobile phase dichloromethane:ethanol=50:1)

Sources & evidence

ORD record
ord-6644c304aa494962bc83c911a283b8e2
Source dataset
uspto-grants-2010_05
Patent number
US07723347B2

Reaction notes

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