Bromine → 3-Bromo-5-methyl-1-tosyl-1h-pyrrolo[2,3-b]pyridine

HRID 1853496Notes

Reaction equation

HRID 1853496 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:5]2=[N:6][CH:7]=1.[Br:21]Br>ClCCl>[Br:21][C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([CH3:1])[CH:3]=2)[N:8]([S:11]([C:14]2[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=2)(=[O:13])=[O:12])[CH:9]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 497589241H-Pyrrolo[2,3-B]pyridine, 5-methyl-1-[(4-methylphenyl)sulfonyl]-

Product 1

HCID 497589793-Bromo-5-methyl-1-tosyl-1h-pyrrolo[2,3-b]pyridineYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-methyl-1-tosyl-1H-pyrrolo[2,3-b]pyridine (1.9 g, 6.62 mmol) in dichloromethane (40 mL) was treated dropwise with a solution of bromine (0.678 mL, 13.24 mmol) in dichloromethane (3 mL). The resulting solution was stirred at room temperature for 3 hours. The reaction mixture was partitioned between dichloromethane (150 mL) and a 1:1 mixture of a saturated aqueous solution of NaHCO3 and a saturated aqueous solution of Na2S2O3 (250 mL). The organic phase was separated and the aqueous phase was re-extracted twice with DCM (50 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo to give the desired compound as an off-white solid (2.381 g, 99% yield). 1H NMR (DMSO-D6, 400 MHz) δ 2.34 (3H, s), 2.39 (3H, s), 7.42 (2H, d), 7.75 (1H, s), 7.99 (2H, d), 8.14 (1H, s), 8.21 (1H, s); MS (ES+) 365.

Workup

  1. customThe reaction mixture was partitioned between dichloromethane (150 mL)
  2. additiona 1:1 mixture of a saturated aqueous solution of NaHCO3
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was re-extracted twice with DCM (50 mL)
  5. dry with materialThe combined organic phases were dried over magnesium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3f22248e380046728b301b06ed91df9b
Source dataset
uspto-grants-2015_02
Patent number
US08962642B2

Reaction notes

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