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Water → 1-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 63596
Notes
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Reaction equation

HRID 63596 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].[C:14]1([S:20](Cl)(=[O:22])=[O:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>C(Cl)Cl.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1>[I:1][C:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([Br:11])[CH:9]=2)[N:4]([S:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:22])=[O:21])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 24758Sodium hydrideHCID 242292125-Bromo-3-iodo-1H-pyrrolo(2,3-b)pyridine

Product 1

HCID 242292401-Benzenesulfonyl-5-bromo-3-iodo-1H-pyrrolo[2,3-b]pyridineYield 97%

Reagents, catalysts & solvents 2

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-iodo-5-bromo-1H-pyrrolo[2,3-b]-pyridine (500 mg, 1.55 mmol) in CH2Cl2 (4.1 ml) are added 60% sodium hydride (186 mg, 4.66 mmol) and benzyltriethylammonium chloride (8 mg, 0.03 mmol) under argon at 0° C. After 30 minutes, benzenesulfonyl chloride (240 μl, 1.86 mmol) is added at 0° C. and the mixture is stirred at room temperature for 2 hours. The mixture is neutralized with water and extracted several times with CH2Cl2. The organic phases are combined, dried on MgSO4 and concentrated under reduced pressure. The residue is precipitated with methanol and the resulting solid filtered to yield the expected product in the form of a pink solid with 97% yield.

Workup

  1. extractionextracted several times with CH2Cl2
  2. customdried on MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue is precipitated with methanol
  5. filtrationthe resulting solid filtered

Sources & evidence

ORD record
ord-faf9dfce3a37438cadf96c5d0cd1079a
Source dataset
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09447093B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes