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

HRID 576278Notes

Reaction equation

HRID 576278 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-547b6bf38b4e417aa28a5e9355d2cbd1
Source dataset
uspto-grants-2015_05
Patent number
US09035047B2

Reaction notes

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