HCID 22676789, compound → HCID 22676765, compound

HRID 1006252Notes

Reaction equation

HRID 1006252 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1)[C:13]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[C:12]2[C:31]1[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH3:39])=[CH:33][CH:32]=1)C1C=CC=CC=1>C(OCC)(=O)C.[Pd]>[CH2:38]([O:37][C:34]1[CH:35]=[CH:36][C:31]([C:12]2[C:11]3[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=3)[N:14]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)[C:13]=2[C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:32][CH:33]=1)[CH3:39]

Participants

4

Reactant 1

HCID 22676789HCID 22676789, compound

Product 1

HCID 22676765HCID 22676765, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of ethyl 5-(benzyloxy)-3-(4-ethoxyphenyl)-1-(4-fluorobenzyl)-1H-indole-2-carboxylate (Example 69, 4.7 g, 9.0 mmol) in ethyl acetate (15 mL) was added to a suspension of 10% palladium on charcoal (2.0 g) in ethyl acetate (10 mL). The mixture was placed under an atmosphere of hydrogen (1 atm) and stirred for 16 h. The reaction was filtered through a pad of Celite using ethyl acetate to rinse. Evaporation of the filtrate left 3.5 g (90%) of the desired product. The product had: 1H NMR (300 MHz, acetone-D6) δ 7.98 (s, 1 H), 6.89-7.42 (m, 11 H), 5.81 (s, 2 H), 4.03-4.19 (m, 4 H), 1.41 (t, 3 H), 1.04 (t, 3 H).

Workup

  1. filtrationThe reaction was filtered through a pad of Celite
  2. washto rinse
  3. customEvaporation of the filtrate
  4. waitleft 3.5 g (90%) of the desired product

Sources & evidence

ORD record
ord-54d1261404a345ccbd15be8a93ddbdd4
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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