HCID 22676767, compound → HCID 22676820, compound

HRID 1006274Notes

Reaction equation

HRID 1006274 reaction equation
[CH:1]1[CH2:5][CH2:4][CH2:3][C:2]=1[C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=1)[C:10]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[C:9]2[C:29]1[CH:34]=[CH:33][CH:32]=[C:31](OCC2CC2)[CH:30]=1>C(OCC)(=O)C.[Pd].CCO>[C:2]([C:32]1[CH:33]=[CH:34][C:29]([C:9]2[C:8]3[C:12](=[CH:13][CH:14]=[C:6]([CH:2]4[CH2:1][CH2:5][CH2:4][CH2:3]4)[CH:7]=3)[N:11]([CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH3:23])[CH:17]=3)[C:10]=2[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:30][CH:31]=1)([CH3:6])([CH3:3])[CH3:1]

Participants

5

Reactant 1

HCID 22676767HCID 22676767, compound

Product 1

HCID 22676820HCID 22676820, compoundYield 187.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethyl 5-(1-cyclopenten-2-yl)-3-[3-(cyclopropylmethoxy)phenyl]-1-(3-methoxybenzyl)-1H-indole-2-carboxylate (Example 128, 225 mg, 0.44 mmol) in ethyl acetate (3 mL) and ETOH (3 mL) was added to a slurry of 10% palladium on charcoal (100 mg) in ethyl acetate (2 mL) and EtOH (2 mL). The reaction was placed under hydrogen (1 atm) and stirred for 16 h. The mixture was filtered through a pad of Celite using ethyl acetate to rinse. Evaporation of the filtrate gave 210 mg (93%) of the product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.37-7.53 (m, 6 H), 7.28 (dd, 1 H), 7.19 (dd, 1 H), 6.67-6.82 (m, 3 H), 5.83 (s, 3 H), 4.08 (q, 2 H), 3.75 (s, 3 H), 3.06 (p, 1 H), 1.99-2.06 (m, 2 H), 1.47-1.83 (m, 6 H), 1.40 (s, 9 H), 0.98 (t, 3 H).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. washto rinse
  3. customEvaporation of the filtrate

Sources & evidence

ORD record
ord-c3e3f223ae224a119bb7b97be3a86287
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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