3-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)- → Furo[3,4-b]pyridin-5(7H)-one, 7-[4-(diethylamino)-2-(hexyloxy)phenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl)-

HRID 1253139Notes

Reaction equation

HRID 1253139 reaction equation
[C:1]([C:4]1[C:5]([C:10]([C:12]2[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]([CH2:21][CH3:22])[C:13]=2[CH3:23])=[O:11])=[N:6][CH:7]=[CH:8][CH:9]=1)(O)=[O:2].[CH2:24]([O:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([N:37]([CH2:40][CH3:41])[CH2:38][CH3:39])[CH:32]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>C(OC(=O)C)(=O)C>[CH2:40]([N:37]([CH2:38][CH3:39])[C:33]1[CH:34]=[CH:35][C:36]([C:10]2([C:12]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[N:14]([CH2:21][CH3:22])[C:13]=3[CH3:23])[C:5]3[C:4](=[CH:9][CH:8]=[CH:7][N:6]=3)[C:1](=[O:2])[O:11]2)=[C:31]([O:30][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:32]=1)[CH3:41]

Participants

4

Reactant 2

HCID 1123443-Pyridinecarboxylic acid, 2-((1-ethyl-2-methyl-1H-indol-3-yl)carbonyl)-HCID 20136803N,N-Diethyl-3-(hexyloxy)aniline

Product 1

HCID 14177719Furo[3,4-b]pyridin-5(7H)-one, 7-[4-(diethylamino)-2-(hexyloxy)phenyl]-7-(1-ethyl-2-methyl-1H-indol-3-yl)-

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

Into 200 ml of acetic anhydride, 15.4 g of (1-ethyl-2-methylindol-3-yl) (3-carboxypyridin-2-yl) ketone and 13.7 g of 1-n-hexyloxy-3-diethylaminobenzene were added, and the resultant mixture was stirred for 3 hours to 60° to 65° C. After cooling the reaction mixture to room temperature, the cooled reaction mixture was treated by the same manner as in Synthetic Example 1 and as a result, 18.9 of the objective compound of the melting point of 154° to 156° C. as pale blue crystals was obtained. The elementary analytical data of the product were as follows.

Workup

  1. customthe cooled reaction mixture
  2. additionwas treated by the same manner as in Synthetic Example 1 and as a result, 18.9 of the objective compound of the melting point of 154° to 156° C. as pale blue crystals
  3. customwas obtained

Sources & evidence

ORD record
ord-6f15d9498baa4d0388d7b689f491b285
Source dataset
uspto-grants-1988_05
Patent number
US04747875

Reaction notes

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