Dichloromethane → HCID 22396903, compound

HRID 1370383Notes

Reaction equation

HRID 1370383 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-3ba7f9059d874e0ca241663d1eb5b9c1
Source dataset
uspto-grants-2003_06
Patent number
US06583135B2

Reaction notes

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