HCID 11763485, compound → HCID 11215169, compound

HRID 864529Notes

Reaction equation

HRID 864529 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[CH:14]/[C:15]1[C:23]2[C:18](=[CH:19][C:20]([Cl:25])=[CH:21][C:22]=2[Cl:24])[N:17]([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH3:35])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[C:16]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])/[C:7]([O:9]C(C)(C)C)=[O:8]>C(O)=O>[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1/[C:6](=[CH:14]/[C:15]1[C:23]2[C:18](=[CH:19][C:20]([Cl:25])=[CH:21][C:22]=2[Cl:24])[N:17]([S:26]([C:29]2[CH:30]=[CH:31][C:32]([CH3:35])=[CH:33][CH:34]=2)(=[O:28])=[O:27])[C:16]=1[C:36]([O:38][CH2:39][CH3:40])=[O:37])/[C:7]([OH:9])=[O:8]

Participants

3

Reactant 1

HCID 11763485HCID 11763485, compound

Product 1

HCID 11215169HCID 11215169, compound

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

Combine (E)-2-(thien-2-yl)-3-(1-p-toluenesulfonyl-2-carboethoxy-4,6-dichloroindol-3-yl)propenoic acid, t-butyl ester and formic acid (96%, 20 mL). After 2 hours, evaporate in vacuo to obtain a residue. Triturate with pentane containing a small amount of diethyl ether to obtain a solid. Recrystallize the solid from cyclohexane/ethyl acetate/acetone, filter, and dry to give the title compound: mp 184°-187° C. (dec). 1H NMR (DMSO-d6) δ 13.2 (br s, 1H), 7.92 (d, 1H, J=1.7 Hz), 7.80 (d, 2H, J=8.4 Hz), 7.60 (s, 1H), 7.57 (d, 1H, J=1.7 Hz), 7.44 (d, 2H, J=8.4 Hz), 7.40 (dd, 1H, J=4.7, 1.5 Hz), 6.84-6.8 (m, 2H), 4.14 (q, 2H, J=7.1 Hz), 2.37 (s, 3H), 1.13 (t, 3H, J=7.1 Hz). Elemental Analysis calculated for C25H19Cl2NO6S2 : C, 53.20; H, 3.39; N, 2.48. Found: C, 53.30; H, 3.40; N, 2.41.

Workup

  1. customevaporate in vacuo
  2. customto obtain a residue
  3. customTriturate with pentane containing a small amount of diethyl ether
  4. customto obtain a solid
  5. customRecrystallize the solid from cyclohexane/ethyl acetate/acetone
  6. filtrationfilter
  7. customdry

Sources & evidence

ORD record
ord-a1c3f66df8f6446588335bf3032a0e58
Source dataset
uspto-grants-1996_10
Patent number
US05563157

Reaction notes

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