N-bromobutanimide → HCID 89407709, compound

HRID 1524394Notes

Reaction equation

HRID 1524394 reaction equation
[CH:1]([Si:4]([CH:21]([CH3:23])[CH3:22])([CH:18]([CH3:20])[CH3:19])[N:5]1[C:9]2=[N:10][C:11]([S:14]([Cl:17])(=[O:16])=[O:15])=[CH:12][CH:13]=[C:8]2[CH:7]=[CH:6]1)([CH3:3])[CH3:2].C1C(=O)N([Br:31])C(=O)C1>C(Cl)Cl>[Br:31][C:7]1[C:8]2[C:9](=[N:10][C:11]([S:14]([Cl:17])(=[O:16])=[O:15])=[CH:12][CH:13]=2)[N:5]([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:18]([CH3:20])[CH3:19])[CH:21]([CH3:23])[CH3:22])[CH:6]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimide2×HCID 89407696HCID 89407696, compound

Product 1

HCID 89407709HCID 89407709, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 100-mL recovery flask was charged with 1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-6-sulfonyl chloride (2.11 g, 5.66 mmol) and DCM (28 ml) to give a clear solution. n-Bromosuccinimide (1.108 g, 6.22 mmol) was added in one portion. The resulting mixture was stirred in the dark for 4 h, then an additional portion of n-bromosuccinimide (1.108 g, 6.22 mmol) was added. The mixture was stirred overnight. In the morning, silica gel was added, and the mixture was concentrated. The impregnated silica gel was loaded onto a column, and the column was eluted onto a silica gel column with 0 to 15% EtOAc/Heptane to give 3-bromo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-6-sulfonyl chloride (2.14 g, 4.74 mmol, 84% yield) as a light-yellow solid. 1H NMR (400 MHz, CDCl3) δ=8.08 (d, J=8.3 Hz, 1 H), 7.95 (d, J=8.3 Hz, 1 H), 7.63 (s, 1 H), 1.88 (spt, J=7.5 Hz, 4 H), 1.15 (d, J=7.5 Hz, 18 H).

Workup

  1. customto give a clear solution
  2. stirringThe mixture was stirred overnight
  3. additionIn the morning, silica gel was added
  4. concentrationthe mixture was concentrated
  5. washthe column was eluted onto a silica gel column with 0 to 15% EtOAc/Heptane

Sources & evidence

ORD record
ord-89f50c5cef9c45df86aa4c2917e3006c
Source dataset
uspto-grants-2015_07
Patent number
US09079902B2

Reaction notes

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