Water → 1H-​Pyrrolo[2,​3-​b]​pyridine, 3-​bromo-​5-​fluoro-​1-​[(4-​methylphenyl)​sulfonyl]​-

HRID 1055043Notes

Reaction equation

HRID 1055043 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([F:11])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[S:14](Cl)([C:17]1[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=1)(=[O:16])=[O:15].O>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([F:11])[CH:9]=2)[N:4]([S:14]([C:17]2[CH:23]=[CH:22][C:20]([CH3:21])=[CH:19][CH:18]=2)(=[O:16])=[O:15])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 534125683-Bromo-5-fluoro-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 712513301H-​Pyrrolo[2,​3-​b]​pyridine, 3-​bromo-​5-​fluoro-​1-​[(4-​methylphenyl)​sulfonyl]​-Yield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-bromo-5-fluoro-1H-pyrrolo[2,3-b]pyridine (5.0 g, 23.3 mmol) was dissolved in DMF (37.5 mL) and cooled to 0° C. Sodium hydride (1.5 g, 37.2 mmol) was added and the reaction mixture was stirred for 10 minutes and then treated with tosyl chloride (6.6 g, 34.9 mmol). The mixture was stirred for 30 minutes at 0° C. and then at room temperature for another 90 minutes. The reaction mixture was poured into water (100 mL) and the resulting solid was collected, washed with water and hexanes three times and dried in vacuo to afford 8.26 g of 3-bromo-5-fluoro-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine, 22a: 1H NMR (300 MHz, DMSO-d6) δ 8.48 (s, 1H), 8.31 (s, 1H), 8.01 (d, J=8.3 Hz, 2H), 7.92 (dd, J=8.4, 2.7 Hz, 1H), 7.44 (d, J=8.5 Hz, 2H), 2.35 (s, 3H).

Workup

  1. stirringThe mixture was stirred for 30 minutes at 0° C.
  2. waitat room temperature for another 90 minutes
  3. customthe resulting solid was collected
  4. washwashed with water and hexanes three times
  5. customdried in vacuo

Sources & evidence

ORD record
ord-9b76740955354210a9331abef05e4599
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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