HCID 67157983, compound → HCID 67158669, compound

HRID 1835228Notes

Reaction equation

HRID 1835228 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH:5]=[CH:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[C:17]1[N:25]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)[CH3:2]>[Pd]>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH3:16])[CH:11]=[C:10]2[C:17]1[N:25]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:27])=[O:28])[C:20]2=[N:21][CH:22]=[CH:23][CH:24]=[C:19]2[CH:18]=1)[CH3:2]

Participants

3

Reactant 1

HCID 67157983HCID 67157983, compound

Product 1

HCID 67158669HCID 67158669, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Palladium (15.7 mg, 10% on activated carbon) was added to a suspension of 3-{1-methyl-3-[1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-1H-indol-5-yl}-acrylic acid ethyl ester [100 mg, Reference Example 37] in industrial methylated spirit (25 mL). The resultant suspension was then stirred under an atmosphere of hydrogen for 16 hours. The reaction mixture was then filtered through a pad of celite and the filtrate evaporated in vacuo. The resultant solid was triturated with water, filtered and dried to give the title compound (92 mg) as a white solid, m.p. 280-282° C. MS: 502 (MH+).

Workup

  1. filtrationThe reaction mixture was then filtered through a pad of celite
  2. customthe filtrate evaporated in vacuo
  3. customThe resultant solid was triturated with water
  4. filtrationfiltered
  5. customdried

Sources & evidence

ORD record
ord-c211831e90bd49e8a259adcbb2ff7e6e
Source dataset
uspto-grants-2004_08
Patent number
US06770643B2

Reaction notes

Loading…