Dichloromethane → HCID 68909689, compound

HRID 2079899Notes

Reaction equation

HRID 2079899 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[CH:15][CH:14]=3)=[CH:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.C(Cl)Cl.Cl.[N:32]1[CH:37]=[CH:36][CH:35]=[C:34]([S:38](Cl)(=[O:40])=[O:39])[CH:33]=1>CN(C)C1C=CN=CC=1.CN(C)C=O>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([C:8]([C:13]3[CH:14]=[CH:15][C:16]([C:17]#[N:18])=[CH:19][CH:20]=3)=[CH:9][N:10]2[S:38]([C:34]2[CH:33]=[N:32][CH:37]=[CH:36][CH:35]=2)(=[O:40])=[O:39])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 12571517Pyridine-3-sulfonyl chloride hydrochlorideHCID 574421974-(6-nitro-1H-indol-3-yl)-benzonitrile

Product 1

HCID 68909689HCID 68909689, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Method N Combine 4-(6-nitro-1H-indol-3-yl)-benzonitrile, 9, (290 mg, 1.1 mmol), 4-dimethylaminopyridine (14 mg, 0.11 mmol), triethyl amine (740 μL, 5.3 mmol), methylene chloride (7.0 mL) and dimethylformamide (2.5 mL) in a 25 mL flask. Add 3-pyridine sulfonyl chloride hydrochloride (283 mg, 1.32 mmol). Let the solution stir overnight. Isolate the precipitate by filtration and wash the precipitate 3× with methylene chloride to yield 251 mg, 0.62 mmol, 56% of the title compound. LRMS (API ES+)=405.0 (M+H).

Workup

  1. customIsolate the precipitate
  2. filtrationby filtration
  3. washwash the precipitate 3× with methylene chloride

Sources & evidence

ORD record
ord-d5b44df4f24348458faa273d792f3415
Source dataset
uspto-grants-2011_04
Patent number
US07932284B2

Reaction notes

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