Acetic Acid → HCID 18914242, compound

HRID 1292383Notes

Reaction equation

HRID 1292383 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([OH:31])=[CH:27][CH:26]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:5]=[C:6]([CH3:8])[CH:7]=1.C([O:34][CH:35]1[CH2:39][CH2:38][CH2:37]O1)C.C(O)(=O)C.[H][H]>[OH-].[OH-].[Pd+2].C(N(CC)CC)C>[CH3:8][C:6]1[CH:5]=[C:4]([C:9]2[NH:10][C:11]3[C:16]([C:17]=2[CH2:18][CH2:19][N:20]([CH2:37][CH2:38][CH2:39][CH2:35][OH:34])[CH2:21][CH2:22][CH2:23][CH2:24][C:25]2[CH:26]=[CH:27][C:28]([OH:31])=[CH:29][CH:30]=2)=[CH:15][CH:14]=[CH:13][CH:12]=3)[CH:3]=[C:2]([CH3:1])[CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 433892-EthoxytetrahydrofuranHCID 9979079HCID 9979079, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18914242HCID 18914242, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8471TriethylamineSolvent

Procedure

To a solution of 4-[4-[[2-[2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl]amino]butyl]phenol (18 mg in 2 mL tetrahydrofuran) was added 0.050 mL of 2-ethoxytetrahydrofuran followed by 0.25 mL of 30% aqueous acetic acid and the mixture stirred for 30 minutes. At this time 0.35 mL triethylamine was added followed by 10% palladium hydroxide on carbon catalyst. The reaction flask was fitted with a hydrogen balloon, evacuated and recharged with hydrogen (3 times) and stirred at room temperature. After 23 hours the reaction was flushed with nitrogen, filtered over diatomaceous earth and concentrated in vacuo and partially purified by flash chromatography on silica gel (methylene chloride:methanol, 92:8). Repurification by HPLC (C8, methanol:water, 55:45=0.1% trifluoroacetic acid) gave the title compound (2.8 mg). m/e=485 (M+H)

Workup

  1. customevacuated
  2. stirringstirred at room temperature
  3. customAfter 23 hours the reaction was flushed with nitrogen
  4. filtrationfiltered over diatomaceous earth
  5. concentrationconcentrated in vacuo
  6. custompartially purified by flash chromatography on silica gel (methylene chloride:methanol, 92:8)
  7. customRepurification by HPLC (C8, methanol:water, 55:45=0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-e889cff0cb1649bfa8def826e378091e
Source dataset
uspto-grants-1998_05
Patent number
US05756507

Reaction notes

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