Dichloromethane → HCID 22396903, compound

HRID 1356256Notes

Reaction equation

HRID 1356256 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:20])[C:14]=2[C:13]2[CH2:21][CH2:22][N:23](C(OC(C)(C)C)=O)[CH2:24][CH2:25][C:12]1=2.FC(F)(F)C(O)=O.C(Cl)[Cl:41]>>[ClH:41].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][N:11]1[C:19]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:20])[C:14]=2[C:13]2[CH2:21][CH2:22][NH:23][CH2:24][CH2:25][C:12]1=2

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 6422Trifluoroacetic acidHCID 22396564HCID 22396564, compound

Product 1

HCID 22396903HCID 22396903, compound

Procedure

tert-Butyl 6-(1H-benzimidazol-2-ylmethyl)-10-bromo-1,4,5,6-tetrahydroazepino[4,5-b]indole-3(2H)-carboxylate (0.105 g, 0.212 mmol) was dissolved in CH2Cl2 (5 mL) and trifluoroacetic acid (2.0 mL, 2.96 g, 26.0 mmol, 122 equiv.) was added. This mixture was stirred at rt in a capped vessel for 2.5 h. The reaction mixture was concentrated to dryness. The residue was taken up in EtOAc (2 mL), and 1M HCl in Et2O was added. The hydrochloride salt was collected by filtration and dried under vacuum. 6-(1H-benzimidazol-2-ylmethyl)-10-bromo-1,2,3,4,5,6-hexahydroazepino[4,5-b]indole hydrochloride (0.943 g) was produced in quantitative yield. 1H NMR (300 MHz, DMF) δ 3.61-3.70, 3.83-3.86, 6.12, 7.06, 7.31, 7.36-7.42, 7.66-7.74, 7.74; 1H NMR (300 MHz, CD3OD) δ 3.33-3.36, 3.54-3.59, 3.83-3.86, 6.04, 7.09, 7.35, 7.41, 7.54-7.57, 7.71-7.74; MS (ESI+) for C20H19BrN4 m/z 395, 396.9 (M+H)+.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. addition1M HCl in Et2O was added
  3. filtrationThe hydrochloride salt was collected by filtration
  4. customdried under vacuum

Sources & evidence

ORD record
ord-cc46bd59504440659154cf3ca001464d
Source dataset
uspto-grants-2003_07
Patent number
US06586421B2

Reaction notes

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