Ammonium formate → HCID 59599679, compound

HRID 985645Notes

Reaction equation

HRID 985645 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH3:17])=[CH:9]1)=O)(C)(C)C.[CH:18]([O-:20])=O.[NH4+]>CO.[Pd]>[O:20]([C:14]1[CH:15]=[C:16]2[C:11]([CH2:10][CH2:17][CH2:9][NH:8]2)=[CH:12][CH:13]=1)[C:18]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 11806510tert-Butyl 3-methyl-1H-indole-1-carboxylate

Product 1

HCID 59599679HCID 59599679, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A well-stirred solution of Compound 7, where R1 is phenyl, R2A is benzyl, R3 is 3-methyl-indole-1-carboxylic acid tert-butyl ester and R4 is methyl, (0.1 g, 0.189 mmol) and ammonium formate (0.06 g 0.945 mmol) in 3 ml of MeOH in a capped vial was treated with 0.05 g of solid 10% palladium on charcoal. The mixture was heated at 60° C. for 1 h with stirring, filtered through celite bed and washed with MeOH. The crude product was further purified by filtration through a silica plug, washing with CH2Cl2/MeOH (20/1) to afford the 7-phenoxy-3,4-dihydro-2H-quinoline-4-spiro-5′-3′-(1H-indol-2-ylmethyl-1-carboxylic acid tert-butyl ester)-1′-methyl-imidazolidine-21, 4′-dione as a colorless oil in quantitative yields. 1H NMR (CDCl3) δ 8.13-8.02 (m, 2H); 7.76-7.64 (m, 2H); 7.35-6.90 (m, 9H); 6.63-6.60 (m, 1H); 6.17-6.12 (m, 2H); 4.81 (s, 2H); 4.18-3.91 (m, 2H); 3.77 (bs, 1H); 3.33-3.27 (m, 1H); 2.70 (s, 3H); 2.29-1.90 (m, 22H); 1.64 (s, 9H).

Workup

  1. filtrationfiltered through celite bed
  2. washwashed with MeOH
  3. filtrationThe crude product was further purified by filtration through a silica plug
  4. washwashing with CH2Cl2/MeOH (20/1)

Sources & evidence

ORD record
ord-9973ab1ba0d946f6937e093e888aa964
Source dataset
uspto-grants-2005_03
Patent number
US06872827B2

Reaction notes

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