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

HRID 2199749Notes

Reaction equation

HRID 2199749 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-2dfd7137fc8e4c65a94a298db5ea79fc
Source dataset
uspto-grants-2016_06
Patent number
US09359296B2

Reaction notes

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