Hydrochloric Acid → HCID 67101076, compound

HRID 2079906Notes

Reaction equation

HRID 2079906 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=3)[C:9]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)=[CH:8]2)[CH2:3][CH2:2]1.C([O-])([O-])=O.[Cs+].[Cs+].[N+](C1C=C2C(C(C3C=CC(C#N)=CC=3)=CN2)=CC=1)([O-])=O.CC1C=C[C:57]([S:60](OC2CCOCC2)(=[O:62])=[O:61])=CC=1.Cl>CN(C=O)C>[O:1]1[CH2:6][CH2:5][CH:4]([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[C:13]([NH:16][S:60]([CH3:57])(=[O:62])=[O:61])[CH:14]=3)[C:9]([C:19]3[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][CH:20]=3)=[CH:8]2)[CH2:3][CH2:2]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 13961807Tetrahydro-2H-pyran-4-yl 4-methylbenzenesulfonateHCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrileHCID 67101262HCID 67101262, compound

Product 1

HCID 67101076HCID 67101076, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-(1-(4-tetrahydropyranyl)-6-nitro-1H-indol-3-yl)-benzonitrile: Add Cs2CO3 (2.54 g, 7.8 mmol) to a mixture of 4-(6-nitro-1H-indol-3-yl)-benzonitrile (1.591 g, 6 mmol), 4-(4-methylphenylsulfonyloxy)tetrahydropyran (2 g, 7.8 mmol) in DMF (25 ml) and under N2 atmosphere; heat the resulting mixture to 60° C. for 14 hours. After cooling, the reaction is poured into ice/water (200 ml) and 5N HCl (6 ml), sonicated, and filtered with Et2O wash to give 1:1 mixture of the title compound:starting material as a brownish red solid (1.202 g).

Workup

  1. temperatureAfter cooling
  2. customsonicated
  3. filtrationfiltered with Et2O
  4. washwash
  5. customto give

Sources & evidence

ORD record
ord-4ffb68218f3343cc9e174a24ec8da609
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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