Cesium fluoride → HCID 86728250, compound

HRID 1776843Notes

Reaction equation

HRID 1776843 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.[F-].[Cs+].[N+](C1C=C(S(O[CH2:33][CH:34]2[CH2:36][O:35]2)(=O)=O)C=CC=1)([O-])=O>CN(C=O)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH2:33][CH:34]2[CH2:36][O:35]2)=[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

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 286836(Oxiran-2-yl)methyl 3-nitrobenzene-1-sulfonateHCID 13163448HCID 13163448, compound

Product 1

HCID 86728250HCID 86728250, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of compound 4-bromo-2-(1H-indol-2-yl)phenol (1 g, 3.48 mmol) in DMF (35 mL) was added CsF (1.59 g, 10.45 mmol) and oxiran-2-ylmethyl 3-nitrobenzenesulfonate (1.81 g, 6.97 mmol). The resulting mixture was stirred at room temperature overnight and then diluted with ethyl acetate and washed with water and brine. The crude product was purified using chromatography (petroleum ether:EA=14:1) to provide compound 2-(5-bromo-2-(oxiran-2-ylmethoxy)phenyl)-1H-indole (1 g, yield: 84.0%). 1H-NMR (DMSO-d6, 400 MHz) δ 11.33 (s, 1H), 7.96 (d, J=2.4 Hz, 1H), 7.51 (d, J=7.6 Hz, 1H), 7.38˜7.44 (m, 2H), 7.07˜7.12 (m, 3H), 6.97 (t, J=7.2 Hz, 1H), 4.49˜4.53 (m, 1H), 3.97˜4.01 (m, 1H), 3.46˜3.49 (m, 1H), 2.88 (t, J=4.4 Hz, 1H), 2.74˜2.76 (m, 1H). MS (M+H)+: 344/346.

Workup

  1. washwashed with water and brine
  2. customThe crude product was purified

Sources & evidence

ORD record
ord-11acd117b9b04d6fa7ef1b971816b4a5
Source dataset
uspto-grants-2016_02
Patent number
US09265773B2

Reaction notes

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