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

HRID 732823
Notes
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Reaction equation

HRID 732823 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 hydroxideCatalyst
HCID 887
Methanol
Solvent
HCID 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-12adc5985d804beca026cf62c3795e02
Source dataset
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07585977B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes