Chlorosuccinimide → HCID 71295631, compound

HRID 1776873Notes

Reaction equation

HRID 1776873 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([CH:17]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1.C1C(=O)N([Cl:25])C(=O)C1>CN(C=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[Cl:25])=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13163448HCID 13163448, compound

Product 1

HCID 71295631HCID 71295631, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-2-(1H-indol-2-yl)phenol (100 mg, 0.35 mmol) in DMF (1 mL) was added NCS (46 mg, 0.35 mmol), it was allowed to stir at room temperature until LCMS showed the starting material was consumed completely. The reaction solution was extracted with EtOAc, and the combined organic layers were washed with H2O (3×10 mL), brine and dried over Na2SO4. The solvent was removed and the crude product was purified using prep-TLC to provide the desired product of 4-bromo-2-(3-chloro-1H-indol-2-yl)phenol (110 mg, yield: 98.2%). 1H-NMR (CDCl3, 400 MHz) δ 9.25 (s, 1H), 7.80 (d, J=2.4 Hz, 1H), 7.64 (d, J=8.0 Hz, 1H), 7.40˜7.43 (m, 1H), 7.20˜7.30 (m, 2H), 7.12 (t, J=4.0 Hz, 1H), 6.86 (t, J=6.0 Hz, 1H), 5.93 (s, 1H). MS (M+H)+: 322/324.

Workup

  1. customwas consumed completely
  2. extractionThe reaction solution was extracted with EtOAc
  3. washthe combined organic layers were washed with H2O (3×10 mL), brine
  4. dry with materialdried over Na2SO4
  5. customThe solvent was removed
  6. customthe crude product was purified

Sources & evidence

ORD record
ord-32e2cbe0915c4d8190642fe08454f854
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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