Pyridine → HCID 67271996, compound

HRID 1696503Notes

Reaction equation

HRID 1696503 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13](B(O)O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)([O:3][C:4]([CH3:7])(C)C)=[O:2].N1C=CC=CC=1.[C:26]([C:30]1[CH:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[NH:32][N:31]=1)([CH3:29])([CH3:28])[CH3:27].B(O)O>C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[C:26]([C:30]1[CH:34]=[C:33]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[N:32]([C:13]2[CH:12]=[C:11]3[C:16](=[CH:15][CH:14]=2)[N:8]([C:1]([O:3][CH2:4][CH3:7])=[O:2])[CH:9]=[CH:10]3)[N:31]=1)([CH3:29])([CH3:27])[CH3:28]

Participants

7

Reactant 4

HCID 1049PyridineHCID 61668Boronic AcidHCID 2743509Ethyl 3-tert-butyl-1H-pyrazole-5-carboxylateHCID 18375637[1-(tert-Butoxycarbonyl)-1H-indol-5-yl]boronic acid

Product 1

HCID 67271996HCID 67271996, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Commercially available N-Boc-5-indoleboronic acid (0.30 g, 1.1 mmol) was dissolved in CH2Cl2 (20 mL) and pyridine (1 mL) with molecular sieves (activated 4 A) and stirred overnight at RT. Commercially available ethyl 3-t-butyl-1 H-pyrazole-5-carboxylate, Cu(OAc)2 and molecular sieves (4 A activated, powder) were added to the boronic acid solution and the whole stirred at RT open to the atmosphere for 2d. The reaction mixture was filtered through a pad of Celite®, concentrated and purified by column chromatography to yield ethyl 5-(3-t-butyl-5-(ethoxycarbonyl)-1H-pyrazol-1-yl)-1H-indole-1-carboxylate (0.18 g, 38% yield). LC-MS (EI) m/z: 412.3 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through a pad of Celite®
  2. concentrationconcentrated
  3. custompurified by column chromatography

Sources & evidence

ORD record
ord-adf4700677e44341bb9c95dc7abe6a7c
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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