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

HRID 2171840Notes

Reaction equation

HRID 2171840 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-b3f0e8af49184403b5730d51ab99e6d8
Source dataset
uspto-grants-2015_06
Patent number
US09051319B2

Reaction notes

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