HCID 68683853, compound → 4-(2-[1-benzhydryl-5-chloro-2-(2-{[(2-hydroxyphenyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethoxy}benzoic acid

HRID 2237129Notes

Reaction equation

HRID 2237129 reaction equation
[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][O:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=2)=[C:15]1[CH2:37][CH2:38][NH:39][S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[O:49]CC1C=CC=CC=1)(=[O:42])=[O:41])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.CCO.[Pd]>[CH:1]([N:14]1[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[C:16]([CH2:24][CH2:25][O:26][C:27]2[CH:36]=[CH:35][C:30]([C:31]([OH:33])=[O:32])=[CH:29][CH:28]=2)=[C:15]1[CH2:37][CH2:38][NH:39][S:40]([C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][C:44]=1[OH:49])(=[O:41])=[O:42])([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 1

HCID 68683853HCID 68683853, compound

Product 1

HCID 219622474-(2-[1-benzhydryl-5-chloro-2-(2-{[(2-hydroxyphenyl)sulfonyl]amino}ethyl)-1H-indol-3-yl]ethoxy}benzoic acidYield 104.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

Methyl 4-(2-{1-benzhydryl-2-[2-(2-benzyloxy-benzenesulfonylamino)-ethyl ]-5-chloro-1H-indol-3-yl}-ethoxy)-benzoate (0.55 g, 0.70 mmol), (Step 1, Example 184) and 10% Pd/C (55 mg) in MeOH (30 ml) and EtOH (20 ml) was hydrogenated. The resulting mixture was filtered through Celite and concentrated. The residue was chromatographed with 35-40% EtOAC/hexane to give the desired product (0.50 g, 95%).

Workup

  1. filtrationThe resulting mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe residue was chromatographed with 35-40% EtOAC/hexane

Sources & evidence

ORD record
ord-e95b6084437f4bc283faffb886953d2e
Source dataset
uspto-grants-2010_05
Patent number
US07713964B2

Reaction notes

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