Triethylamine → HCID 68633737, compound

HRID 1802820Notes

Reaction equation

HRID 1802820 reaction equation
[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:20]Br)=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[C:10]([Br:22])=[C:9]1[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].CCN(CC)CC.[O:36]=[S:37]1(=[O:43])[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1.[NH4+].[Cl-]>C(Cl)Cl>[C:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:20][N:40]3[CH2:41][CH2:42][S:37](=[O:43])(=[O:36])[CH2:38][CH2:39]3)=[CH:14][C:15]=2[N+:17]([O-:19])=[O:18])[C:10]([Br:22])=[C:9]1[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 6484228Thiomorpholine 1,1-dioxideHCID 68472286HCID 68472286, compound

Product 1

HCID 68633737HCID 68633737, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-BOC-3-bromo-5-bromomethyl-7-nitro-2-phenyl-indole (1.0 g, 2 mmol) obtained in Step 2 was dissolved in DCM (10 mL), and thereto Et3N (560 uL, 4 mmol) and 1,1-dioxo-thio-morpholine (300 mg, 3 mmol) were added. The mixture was stirred for 12 hours at room temperature. At the end of the reaction, added saturated aqueous NH4Cl solution, extracted with DCM. After drying the extract, the solvent was removed under reduced pressure and the residue was purified by column chromatography to give 1-BOC-3-bromo-5-(1,1-dioxo-thiomorpholine-4-yl)methyl-7-nitro-2-phenyl-1H-indole (825 mg, 78%).

Workup

  1. customAt the end of the reaction
  2. extractionextracted with DCM
  3. customAfter drying the extract
  4. customthe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cd6f9feab16f4c1b8dbdfe74cfdf9e75
Source dataset
uspto-grants-2013_01
Patent number
US08349885B2

Reaction notes

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