Tetrahydrofuran → HCID 21906932, compound

HRID 1246942Notes

Reaction equation

HRID 1246942 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:18][C:19]([O-])([CH3:21])[CH3:20].[K+].[F:24]C1C=C(C=CC=1)CBr.[CH2:33]1[CH2:37]OC[CH2:34]1>>[F:24][C:18]1[CH:37]=[CH:33][CH:34]=[CH:21][C:19]=1[CH2:20][N:14]1[C:15]2[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:17][CH:16]=2)[CH:12]=[CH:13]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 146245-BenzyloxyindoleHCID 680073-Fluorobenzyl bromideHCID 23665647Potassium tert-butoxide

Product 1

HCID 21906932HCID 21906932, compoundYield 44%

Procedure

5-Benzyloxyindole (500 mg, 2.24 mmol) was dissolved in THF (20 mL) and treated with 1M KOtBu in THF (2.24 mL, 2.24 mmol). After stirring for 3 hours, 3-fluorobenzyl bromide (274 μL, 2.24 mmol) was added and the reaction mixture was stirred for an additional 24 hrs. Standard aqueous workup and purification by silica gel chromatography, eluting with 5:1 hexanes/ethyl acetate, provided N-(2-fluorobenzyl)-5-benzyloxyindole (325 mg, 44%). 1H NMR (200 MHz, CDCl3) δ 7.55–7.29 (mn, 5H), 7.28–7.05 (m, 3H), 7.04–6.81 (m, 5H), 6.49 (dd, J=0.7, 3.1 Hz, 1H), 5.26 (s, 2H), 5.10 (s, 2H). MS (EI, m/z) M+=33 1.

Workup

  1. stirringthe reaction mixture was stirred for an additional 24 hrs
  2. customStandard aqueous workup and purification by silica gel chromatography
  3. washeluting with 5:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-14d18fcb8f754abe8868b906f6af19b1
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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