5-Benzyloxyindole → HCID 69663370, compound

HRID 1246943Notes

Reaction equation

HRID 1246943 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+].BrC[N:26]1[C:30](=[O:31])C2=CC=[CH:34][CH:35]=[C:28]2[C:27]1=[O:36]>C1COCC1>[CH2:18]=[C:19]1[CH:21]=[CH:34][CH:35]=[C:28]2[C:27]([N:26]([N:14]3[C:15]4[C:11](=[CH:10][C:9]([O:8][CH2:1][C:2]5[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=5)=[CH:17][CH:16]=4)[CH:12]=[CH:13]3)[C:30](=[O:31])[CH:20]12)=[O:36]

Participants

5

Reactant 3

HCID 146245-BenzyloxyindoleHCID 792441H-Isoindole-1,3(2H)-dione, 2-(bromomethyl)-HCID 23665647Potassium tert-butoxide

Product 1

HCID 69663370HCID 69663370, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

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, N-(bromomethyl) phthalimide (538 mg, 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 3:1 hexane/ethyl acetate, provided N-(methylenephthalimido)-5-benzyloxyindole (650 mg, 76%). 1H NMR (200 MHz, CDCl3) δ 7.83 (d, J=5.5 Hz, 1H), 7.81 (d, J=5.5 Hz, 1H), 7.72–7.65 (m, 2H), 7.45 (m, 1H), 7.42 (d, 3.0 Hz, 2H), 7.40–25 (m, 2H), 7.09 (d, J=2.2 Hz, 1H), 7.00 (dd, J=2.2, 9.0 Hz, 1H), 6.49 (d, J=3.2 Hz, 1H), 5.91 (s, 2H), 5.07 (s, 2H). MS (EI. m/z) M+=382.

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 3:1 hexane/ethyl acetate

Sources & evidence

ORD record
ord-a2251e09bf5d42b5864d96753cb05a08
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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