Benzyl 4-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxy phenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoate → 4-(1-(4-(1,3-Dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxyphenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoic acid

HRID 1952533Notes

Reaction equation

HRID 1952533 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([C:27]3[S:28][C:29]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=4)=[C:30]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=3)=[O:26])[CH:23]=2)[CH:18]=[C:17]1[C:45]1[CH:60]=[CH:59][C:48]([C:49]([O:51]CC2C=CC=CC=2)=[O:50])=[CH:47][CH:46]=1>CO.CCOC(C)=O.[Pd]>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][CH2:14][CH2:15][N:16]1[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:25]([C:27]3[S:28][C:29]([C:38]4[CH:43]=[CH:42][CH:41]=[C:40]([OH:44])[CH:39]=4)=[C:30]([CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])[CH:31]=3)=[O:26])[CH:23]=2)[CH:18]=[C:17]1[C:45]1[CH:46]=[CH:47][C:48]([C:49]([OH:51])=[O:50])=[CH:59][CH:60]=1

Participants

5

Reactant 1

HCID 67497144Benzyl 4-(1-(4-(1,3-dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxy phenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoate

Product 1

HCID 674967264-(1-(4-(1,3-Dioxoisoindolin-2-yl)butyl)-6-(4-(2-ethoxy-2-oxoethyl)-5-(3-hydroxyphenyl)thiophene-2-carbonyl)-1H-indol-2-yl)benzoic acidYield 88%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 6 (50 mg, 0.061 mmol) and 10% Pd—C (20 mg) in MeOH (8 mL) and EtOAc (3 mL) was stirred under 1 atm H2 atmosphere until 6 was no longer detected by TLC. The resulting solution was filtered and concentrated in vacuo to give 7 as a yellow amorphous solid (39 mg, 88%). 1H NMR (400 MHz, CDCl3) δ 8.16 (d, J=8.4 Hz, 2H), 8.06 (s, 1H), 7.77-7.65 (m, 7H), 7.59 (d, J=8.0 Hz, 2H), 7.29 (t, J=8.0 Hz, 2H), 7.11 (s, 1H), 7.03 (d, J=7.6 Hz, 1H), 6.93 (d, J=8.0 Hz, 1H), 6.66 (s, 1H), 4.34 (brt, 2H), 4.15 (q, J=7.2 Hz, 2H), 3.72 (s, 2H), 3.52 (brt, 2H), 1.72-1.65 (m, 2H), 1.51-1.47 (m, 2H), and 1.24 (t, J=7.2 Hz, 3H); 13C NMR (100 MHz, CDCl3) δ 188.63, 171.67, 170.53, 168.73, 157.13, 149.52, 143.65, 141.52, 137.98, 137.73, 137.34, 134.34, 134.25, 131.97, 131.89, 131.84, 130.82, 130.56, 130.40, 129.55, 129.37, 123.54, 121.93, 121.17, 120.89, 116.52, 116.44, 112.83, 104.34, 61.59, 43.97, 37.38, 34.90, 27.46, 25.84, and 14.40.

Workup

  1. filtrationThe resulting solution was filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc85637b30a3406e8d177c21d8bbd675
Source dataset
uspto-grants-2013_03
Patent number
US08404728B2

Reaction notes

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