2,3-Dimethyl-1H-indol-5-ol → 6-Cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline

HRID 2222396Notes

Reaction equation

HRID 2222396 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]3)=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[CH3:26][C:27]1[NH:28][C:29]2[C:34]([C:35]=1[CH3:36])=[CH:33][C:32]([OH:37])=[CH:31][CH:30]=2>>[C:12]([C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][S:21](=[O:25])(=[O:24])[CH2:20][CH2:19]1)[N:5]=[CH:4][CH:3]=[C:2]2[O:37][C:32]1[CH:33]=[C:34]2[C:29](=[CH:30][CH:31]=1)[NH:28][C:27]([CH3:26])=[C:35]2[CH3:36])#[N:13]

Participants

3

Reactant 2

HCID 220307882,3-Dimethyl-1H-indol-5-olHCID 597122364-Chloro-6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline

Product 1

HCID 101419726-Cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)quinolineYield 64.8%

Procedure

Using an analogous procedure to that described in Example 7, 4chloro-6-cyano-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline (100 mg, 0.26 mmol) was reacted with 2,3-dimethyl-5-hydroxyindole (51 mg, 0.32 mmol), (Arch. Pharm. 1972, 305, 159), to give 6-cyano-4-(2,3-dimethylindol-5-yloxy)-7-(3-(1,1-dioxothiomorpholino)propoxy)quinoline (85 mg, 64%).

Sources & evidence

ORD record
ord-5f0b9cc12062495d967a22972135edf5
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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