Tetrahydrofuran → HCID 68426173, compound

HRID 225982Notes

Reaction equation

HRID 225982 reaction equation
C([O:8][C:9]1[CH:56]=[CH:55][CH:54]=[CH:53][C:10]=1[CH2:11][S:12]([NH:15][CH2:16][CH2:17][C:18]1[N:19]([CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:20]2[C:25]([C:26]=1[CH2:27][CH2:28][O:29][C:30]1[CH:38]=[CH:37][C:33]([C:34]([OH:36])=[O:35])=[CH:32][CH:31]=1)=[CH:24][C:23]([Cl:39])=[CH:22][CH:21]=2)(=[O:14])=[O:13])C1C=CC=CC=1.[CH2:57]1COCC1>[Pd].CO>[CH3:57][O:36][C:34](=[O:35])[C:33]1[CH:37]=[CH:38][C:30]([O:29][CH2:28][CH2:27][C:26]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([Cl:39])[CH:24]=3)[N:19]([CH:40]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=3)[C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:18]=2[CH2:17][CH2:16][NH:15][S:12]([CH2:11][C:10]2[CH:53]=[CH:54][CH:55]=[CH:56][C:9]=2[OH:8])(=[O:13])=[O:14])=[CH:31][CH:32]=1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 15950152HCID 15950152, compound

Product 1

HCID 68426173HCID 68426173, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 4-{2-[2-[2-({[2-(benzyloxy)benzyl]sulfonyl}amino)ethyl]-5-chloro-1-(diphenylmethyl)-1H-indol-3-yl]ethoxy}benzoic acid (Step 9, Example 1, 109 mg, 0.14 mmol) was added THF and MeOH. 10% of Pd/C (11 mg) was added. The mixture was stirred at room temperature under H2 (1 atm) overnight and filtered through celite, concentrated, and column chromatographed (35% EtOAc/hex) to give 4-(2-{1-benzhydryl-5-chloro-2-[2-(2-hydroxy-phenylmethanesulfonylamino)-ethyl]-1H-indol-3-yl}-ethoxy)-benzoic acid methyl ester (74 mg, 76%), an off-white solid.

Workup

  1. filtrationfiltered through celite,
  2. concentrationconcentrated
  3. customcolumn chromatographed (35% EtOAc/hex)

Sources & evidence

ORD record
ord-e484e435e8bb449da6c38757e78c9d1f
Source dataset
uspto-grants-2009_07
Patent number
US07557135B2

Reaction notes

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