HCID 58117440, compound → HCID 58117344, compound

HRID 1406398Notes

Reaction equation

HRID 1406398 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([O:19]CC3C=CC=CC=3)=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:27]1[C:28](=[O:45])[N:29]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:44])([CH3:43])[CH3:42])[CH:30]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:32]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=2)[CH:10]=[C:9]1[C:27]1[C:28](=[O:45])[N:29]([CH2:37][O:38][CH2:39][CH2:40][Si:41]([CH3:43])([CH3:42])[CH3:44])[CH:30]=[C:31]([C:33]([O:35][CH3:36])=[O:34])[CH:32]=1)=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

4

Reactant 1

HCID 58117440HCID 58117440, compound2×

Product 1

HCID 58117344HCID 58117344, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Conditions

Temperature
30 °C

Procedure

To a degassed solution of intermediate (3d), 2-[5-methoxycarbonyl-2-oxo-1-(2-trimethylsilanyl-ethoxymethyl)-1,2-dihydro-pyridin-3-yl]indole-1,5-dicarboxylic acid 5-benzyl ester 1-tert-butyl ester, (2.07 g, 3.27 mmol) in methanol (30 mL) was added palladium, 10 wt. % on activated carbon (50 mg) and the reaction further degassed. The reaction was heated to 30° C. for 72 hours under a hydrogen atmosphere. The reaction mixture was then filtered through a celite pad and the pad rinsed with hot methanol (20 mL). The combined filtrate and washings were concentrated in vacuo and poured onto 4×10 g PE-AX columns. The columns were then flushed with methanol and eluted with 20% acetic acid/methanol. The combined organics were concentrated in vacuo. To the residue was added ether and this was concentrated in vacuo. This process was repeated twice more and furnished the desired title compound as a brown solid, 627 mg, 35%.

Workup

  1. filtrationThe reaction mixture was then filtered through a celite pad
  2. washthe pad rinsed with hot methanol (20 mL)
  3. concentrationThe combined filtrate and washings were concentrated in vacuo
  4. additionpoured onto 4×10 g PE-AX columns
  5. customThe columns were then flushed with methanol
  6. washeluted with 20% acetic acid/methanol
  7. concentrationThe combined organics were concentrated in vacuo
  8. additionTo the residue was added ether
  9. concentrationthis was concentrated in vacuo

Sources & evidence

ORD record
ord-3108a215ec2640f6b2f8190d5b988d8d
Source dataset
uspto-grants-2014_12
Patent number
US08916591B2

Reaction notes

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