7-Nitroindole → HCID 178526401, compound

HRID 2097666Notes

Reaction equation

HRID 2097666 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[C:12]=1[NH:11][CH:10]=[CH:9]2)([O-])=O.[C:13](Cl)(=[O:17])[C:14](Cl)=[O:15].CCN(C(C)C)C(C)C.[N+:28](C1C=CC=C2C=1NC=C2C(=O)C(Cl)=O)([O-:30])=[O:29]>CCOCC.C1COCC1.O1CCOCC1.C(Cl)Cl>[O:15]=[CH:14][C:13]([NH-:1])=[O:17].[N+:28]([C:10]1[NH:11][C:12]2[C:8]([CH:9]=1)=[CH:7][CH:6]=[CH:5][CH:4]=2)([O-:30])=[O:29]

Participants

9

Reactant 4

HCID 233967-NitroindoleHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 86668736HCID 86668736, compound

Product 1

HCID 178526401HCID 178526401, compound

Reagents, catalysts & solvents 4

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×HCID 8028TetrahydrofuranSolventHCID 312751,4-DioxaneSolvent

Procedure

7-Nitro indole (1 eq.) and oxalyl dichloride (10 eq.) were mixed in ether or CH2Cl2. The reaction was stirred for 24 hours and 2-(7-nitro-1H-indol-3-yl)-2-oxoacetyl chloride precipitated from solution. Filtration offered yellow solid which was dried under vacuum and used in Step 2 without purification. Step 2: iPr2NEt (1-10 eq.) was added into a solution of 2-(7-nitro-1H-indol-3-yl)-2-oxoacetyl chloride from Step 1 and amine (1 eq.) in THF, dioxane or CH2Cl2. The reaction was stirred at room temperature for 24 hours, before being quenched with NaHCO3 (equal volume to THF, dioxane or CH2Cl2 used). The aqueous phase was extracted with EtOAc (3× equal volume to THF, dioxane or CH2Cl2 used). The combined organic phase was dried over MgSO4, filtered and concentrated under vacuum to give a crude product, nitro indole 2-oxoacetyl amide, which was used without purification in the Step 3.

Workup

  1. custom2-(7-nitro-1H-indol-3-yl)-2-oxoacetyl chloride precipitated from solution
  2. filtrationFiltration
  3. customwas dried under vacuum
  4. customused in Step 2 without purification
  5. stirringThe reaction was stirred at room temperature for 24 hours
  6. custombefore being quenched with NaHCO3 (equal volume to THF, dioxane or CH2Cl2 used)
  7. extractionThe aqueous phase was extracted with EtOAc (3× equal volume to THF, dioxane or CH2Cl2 used)
  8. dry with materialThe combined organic phase was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1f58176336c544b181cc92e2d2297faf
Source dataset
uspto-grants-2013_05
Patent number
US08450361B2

Reaction notes

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