Hydrochloric Acid → HCID 58565372, compound

HRID 2175336Notes

Reaction equation

HRID 2175336 reaction equation
Cl.[Br:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[CH:19]([NH:21]C(=O)OC(C)(C)C)[CH3:20]>O1CCOCC1.CCOC(C)=O>[Br:2][C:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[CH:13]=2)[C:4]=1[CH:19]([NH2:21])[CH3:20]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 58565357HCID 58565357, compound

Product 1

HCID 58565372HCID 58565372, compoundYield 102.9%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent2×

Procedure

Hydrogen chloride (4.0 M) in 1,4-dioxane (1.2 mL, 4.8 mmol) was added to a solution of tert-butyl {1-[3-bromo-1-(3-fluorophenyl)-1H-indol-2-yl]ethyl}carbamate (0.15 g, 0.35 mmol) in 1,4-dioxane (2.0 mL) The reaction was stirred at room temperature for 2 hours. The mixture was diluted with EtOAc, washed with saturated NaHCO3 solution, dried over MgSO4 and concentrated to give the crude product (0.12 g). LCMS calculated for C16H12BrFN (M-NH2)+: m/z=316.0. Found: 316.0.

Workup

  1. washwashed with saturated NaHCO3 solution
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-2dac875b091545fdac78c65724420091
Source dataset
uspto-grants-2015_06
Patent number
US09062055B2

Reaction notes

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