Water → 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine

HRID 1034659Notes

Reaction equation

HRID 1034659 reaction equation
[Br:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][N:8]([Si](C(C)C)(C(C)C)C(C)C)[C:5]2=[N:6][CH:7]=1.O.CCOCC>C1COCC1>[Br:1][C:2]1[C:3]([F:21])=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 3283Diethyl EtherHCID 497589465-Bromo-4-fluoro-1-[tris(1-methylethyl)silyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 534129385-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridineYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3H2O (80.8 mL, 80.8 mmol; 1.0M solution in THF) was added to 5-bromo-4-fluoro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (30.0 g, 80.8 mmol) in THF (200 mL) at room temperature. The reaction was stirred for 20 minutes, and then water (200 mL) and ether (500 mL) were added. The aqueous phase was extracted with ether. The combined organic phases were washed with brine, dried (MgSO4) and concentrated in vacuo. The solid was crystallized from EtOAc to provide 5-bromo-4-fluoro-1H-pyrrolo[2,3-b]pyridine (12.5 g, 72% yield). 1H NMR (400 MHz, CDCl3) δ 11.06 (br s, 1H), 8.39 (d, 1H), 7.35 (dd, 1H), 6.60 (dd, 1H); LCMS (APCI+) m/z 214.9, 216.9 (M+H)+, Retention time=2.75 minutes (Method 1).

Workup

  1. extractionThe aqueous phase was extracted with ether
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe solid was crystallized from EtOAc

Sources & evidence

ORD record
ord-efdb4c51c1c1433ab184dccae4617977
Source dataset
uspto-grants-2013_10
Patent number
US08545897B2

Reaction notes

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