Chlorosuccinimide → tert-Butyl 10-chloro-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate

HRID 2423201Notes

Reaction equation

HRID 2423201 reaction equation
[Cl:1]N1C(=O)CCC1=O.[CH3:9][CH:10]1[C:16]2=[C:17]3[C:21](=[CH:22][CH:23]=[C:15]2[O:14][CH2:13][CH2:12][N:11]1[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[NH:20][CH:19]=[CH:18]3>C1COCC1>[Cl:1][C:18]1[C:17]2[C:21](=[CH:22][CH:23]=[C:15]3[O:14][CH2:13][CH2:12][N:11]([C:24]([O:26][C:27]([CH3:29])([CH3:28])[CH3:30])=[O:25])[CH:10]([CH3:9])[C:16]3=2)[NH:20][CH:19]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67242740tert-Butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate2×

Product 1

HCID 67242395tert-Butyl 10-chloro-1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylateYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-chlorosuccinimide (13 mg, 0.10 mmol) was added to a solution of tert-butyl 1-methyl-1,3,4,8-tetrahydro-2H-[1,4]oxazepino[6,7-e]indole-2-carboxylate (Intermediate 42, 0.030 g, 0.099 mmol) in THF (2 mL) and the reaction mixture was stirred at room temperature overnight. The solvent was evaporated and the crude material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN) to give the title compound (17.5 mg) as a white solid. MS m/z 337 [M+H]+.

Workup

  1. customThe solvent was evaporated
  2. customthe crude material was purified by preparative HPLC (XTerra C18, 50 mM NH4HCO3 pH 10-CH3CN)

Sources & evidence

ORD record
ord-60af270033a54d76ac4f84fbec2f90dc
Source dataset
uspto-grants-2011_06
Patent number
US07960374B2

Reaction notes

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