Ammonium formate → 2-(4-(Ethylsulfonyl)phenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)benzo[b]thiophen-6-ol

HRID 748957Notes

Reaction equation

HRID 748957 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([O:17][C:18]3[CH:32]=[CH:31][C:21]([O:22][CH2:23][CH2:24][N:25]4[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]4)=[CH:20][CH:19]=3)=[C:15]([C:33]3[CH:38]=[CH:37][C:36]([S:39]([CH2:42][CH3:43])(=[O:41])=[O:40])=[CH:35][CH:34]=3)[S:14][C:13]=2[CH:44]=1)C1C=CC=CC=1.C([O-])=O.[NH4+]>CO.C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[CH2:42]([S:39]([C:36]1[CH:37]=[CH:38][C:33]([C:15]2[S:14][C:13]3[CH:44]=[C:9]([OH:8])[CH:10]=[CH:11][C:12]=3[C:16]=2[O:17][C:18]2[CH:32]=[CH:31][C:21]([O:22][CH2:23][CH2:24][N:25]3[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]3)=[CH:20][CH:19]=2)=[CH:34][CH:35]=1)(=[O:41])=[O:40])[CH3:43]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 597514231-(2-{4-[6-Benzyloxy-2-(4-ethanesulfonyl-phenyl)-benzo[b]thiophen-3-yloxy]-phenoxy}-ethyl)-piperidine

Product 1

HCID 444274052-(4-(Ethylsulfonyl)phenyl)-3-(4-(2-(piperidin-1-yl)ethoxy)phenoxy)benzo[b]thiophen-6-olYield 87.2%

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Dissolve the compound of Example 87 (400 mg, 0.64 mmol) in methanol (7 mL) and ethyl acetate (7 mL). Add ammonium formate (521 mg, 8.3 mmol) and palladium hydroxide (240 mg) and heat to reflux for 5 hours. Filter the reaction mixture and concentrate in vacuo to give 300 mg of the title compound (86%): mass spectrum (ion spray): m/z=538 (M+H).

Workup

  1. temperatureto reflux for 5 hours
  2. filtrationFilter the reaction mixture
  3. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-eabb459a073f413da1df6328fc9ccfae
Source dataset
uspto-grants-2008_07
Patent number
US07399867B2

Reaction notes

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