Sodium Hydroxide → 5-Bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine

HRID 2375945Notes

Reaction equation

HRID 2375945 reaction equation
C1(S([N:10]2[C:14]3=[N:15][CH:16]=[C:17]([Br:20])[C:18]([Cl:19])=[C:13]3[CH:12]=[C:11]2[I:21])(=O)=O)C=CC=CC=1.BrC1C(Cl)=C2C=C(I)N(S(C3C=CC=CC=3I)(=O)=O)C2=NC=1.[OH-].[Na+]>C1COCC1.CO>[Br:20][C:17]1[C:18]([Cl:19])=[C:13]2[CH:12]=[C:11]([I:21])[NH:10][C:14]2=[N:15][CH:16]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 59854535HCID 59854535, compoundHCID 59854553HCID 59854553, compound

Product 1

HCID 598545525-Bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of a 4:6 mixture of 1-benzenesulfonyl-5-bromo-4-chloro-2-iodo-1H-pyrrolo[2,3-b]pyridine and 5-bromo-4-chloro-2-iodo-1-(2-iodobenzenesulfonyl)-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.178 mmol) in THF (4 mL) was added 3N NaOH in methanol (1 mL), and the mixture was stirred at RT for 30 min. The reaction was quenched with saturated ammonium chloride solution (2 mL), water (5 mL) was added, and the mixture was filtered. The precipitate obtained was washed with water (3×10 mL) followed by hexane (3×10 mL) and dried under vacuum to yield the title compound as white solid. 1H NMR (400 MHz, CD3OD): δ=8.21 (s, 1H), 6.74 (s, 1H); MS (ES+): m/z 358.75 (100) [MH+]; HPLC: tR=5.68 min (ZQ2000, nonpolar—15 min).

Workup

  1. customThe reaction was quenched with saturated ammonium chloride solution (2 mL), water (5 mL)
  2. additionwas added
  3. filtrationthe mixture was filtered
  4. customThe precipitate obtained
  5. washwas washed with water (3×10 mL)
  6. customdried under vacuum

Sources & evidence

ORD record
ord-c24071a974d44a38a20535d554c59a5c
Source dataset
uspto-grants-2008_12
Patent number
US07465726B2

Reaction notes

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