Orcinol → ethyl 7-bromo-3-(3-(3-hydroxy-5-methylphenoxy)propyl)-1H-indole-2-carboxylate

HRID 2095276Notes

Reaction equation

HRID 2095276 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[C:29]2[C:24](=[CH:25]C=CC=2)[CH:23]=[CH:22][CH:21]=1.CC1C=C(O)C=C([OH:37])C=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1C=CC(COC(/N=N/C(OCC2C=CC=CC=2)=O)=O)=CC=1>O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:7]2[CH2:16][CH2:17][CH2:18][O:19][C:20]1[CH:29]=[C:24]([CH3:25])[CH:23]=[C:22]([OH:37])[CH:21]=1

Participants

6

Reactant 4

HCID 10436OrcinolHCID 11776TriphenylphosphineHCID 5387121Dibenzyl azodicarboxylateHCID 68938945ethyl 7-bromo-3-(3-(naphthalen-1-yloxy)propyl)-1H-indole-2-carboxylate

Product 1

HCID 68939274ethyl 7-bromo-3-(3-(3-hydroxy-5-methylphenoxy)propyl)-1H-indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A suspension of ethyl 7-bromo-3-(3-hydroxypropyl)-1H-indole-2-carboxylate (EXAMPLE 1C) (0.9 g), 5-methylbenzene-1,3-diol (1.028 g), triphenylphosphine (0.868 g), dibenzylazodicarboxylate (0.762 g) and tetrahydrofuran (40 ml) was stirred at room temperature for 19 hours. After removal of the solvent, the crude product was purified by flash chromatography silica gel, (Analogix, SF65-200 g) eluting with 0-10% ethyl acetate in hexane.

Workup

  1. customAfter removal of the solvent
  2. customthe crude product was purified by flash chromatography silica gel
  3. wash(Analogix, SF65-200 g) eluting with 0-10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-edb808d9af42418780e96f838ef40df1
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

Loading…