Iodoethane → HCID 25073121, compound

HRID 1096498Notes

Reaction equation

HRID 1096498 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[C:5]3[CH2:20][CH2:21][N:22](C(OC(C)(C)C)=O)[CH:23]([CH3:24])[C:3]=1[C:4]=23.C([O-])([O-])=O.[K+].[K+].[CH2:38](I)[CH3:39]>CC(C)=O>[CH2:38]([O:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[C:5]3[CH2:20][CH2:21][NH:22][CH:23]([CH3:24])[C:3]=1[C:4]=23)[CH3:39]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 59848833HCID 59848833, compound

Product 1

HCID 25073121HCID 25073121, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
62 °C

Procedure

tert-Butyl 7-hydroxy-6-methyl-1-(phenylsulfonyl)-1,3,4,6-tetrahydro-5H-azepino[5,4,3-cd]indole-5-carboxylate, Intermediate 15 (16 mg, 0.036 mmol), acetone (5 mL), K2CO3 (50 mg, 0.36 mmol) and EtI (34 mg, 0.22 mmol) were added into a 16 mm test tube with screw cap and the suspension was stirred at 62° C. over night. The solvent from the filtered mixture was evaporated at reduced pressure and the residue was dissolved in DCM/TFA 50/50 (1 mL) and left in room temperature for two hours. The solvent was evaporated at reduced pressure and the crude was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN) to give 9.0 mg (67%) of the title compound as a brown oil. MS m/z 371 [M+H]+.

Workup

  1. customcap
  2. customThe solvent from the filtered mixture was evaporated at reduced pressure
  3. dissolutionthe residue was dissolved in DCM/TFA 50/50 (1 mL)
  4. customThe solvent was evaporated at reduced pressure
  5. customthe crude was purified by preparative HPLC (Xterra C18, 10 mM NH4CO3 (pH 10)-CH3CN)

Sources & evidence

ORD record
ord-935dd2579de54f1793f54b82cfd334aa
Source dataset
uspto-grants-2012_03
Patent number
US08138333B2

Reaction notes

Loading…