4-Bromobutyryl chloride → HCID 66606703, compound

HRID 661957Notes

Reaction equation

HRID 661957 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:15][CH2:14][C:13]2[C:12]3[C:7](=[C:8]([C:17]([NH2:19])=[O:18])[CH:9]=[CH:10][C:11]=3[Br:16])[NH:6][C:5]=2[CH2:4]1.[Br:20][CH2:21][CH2:22][CH2:23][C:24](Cl)=[O:25]>C1COCC1.C(Cl)Cl>[Br:16][C:11]1[CH:10]=[CH:9][C:8]([C:17]([NH2:19])=[O:18])=[C:7]2[C:12]=1[C:13]1[CH2:14][CH2:15][CH:3]([CH2:2][NH:1][C:24](=[O:25])[CH2:23][CH2:22][CH2:21][Br:20])[CH2:4][C:5]=1[NH:6]2

Participants

5

Reactant 2

HCID 702254-Bromobutyryl chlorideHCID 666059472-(aminomethyl)-5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

Product 1

HCID 66606703HCID 66606703, compoundYield 42.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Step 4 A suspension of 2-(aminomethyl)-5-bromo-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide (130 mg, 0.403 mmol) and TEA (0.067 mL, 0.484 mmol) in THF (2 mL) was treated with 4-bromobutanoyl chloride (74.8 mg, 0.403 mmol). The mixture was stirred at rt for 20 min, diluted with DCM, washed with NaHCO3 (aq), dried and concentrated. The residue was purified by column chromatography (eluting with EtOAc) to provide 5-bromo-2-((4-bromobutanamido)methyl)-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a white solid (80 mg, 42%). Mass spectrum m/z 470, 472, 474 (M+H)+.

Workup

  1. washwashed with NaHCO3 (aq)
  2. customdried
  3. concentrationconcentrated
  4. customThe residue was purified by column chromatography (eluting with EtOAc)

Sources & evidence

ORD record
ord-fa385e049869421b82295c04fc2bec01
Source dataset
uspto-grants-2011_12
Patent number
US08084620B2

Reaction notes

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