Potassium Carbonate → Tert-butyl 4-(3-bromoisoquinolin-1-yl)-1,4-diazepane-1-carboxylate

HRID 1929367Notes

Reaction equation

HRID 1929367 reaction equation
[Br:1][C:2]1[N:3]=[C:4](Br)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[N:13]1([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:19][CH2:18][CH2:17][NH:16][CH2:15][CH2:14]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[N:3]=[C:4]([N:16]2[CH2:17][CH2:18][CH2:19][N:13]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:14][CH2:15]2)[C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 6409761,3-DibromoisoquinolineHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylate

Product 1

HCID 57690659Tert-butyl 4-(3-bromoisoquinolin-1-yl)-1,4-diazepane-1-carboxylateYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of dibromoisoquinoline (150 mg, 0.52 mmol), tert-Butyl 1,4-diazepane-1-carboxylate (104 mg, 0.52 mmol) and potassium carbonate (144 mg, 1.04 mmol) in DMF (5 ml) was heated to 90° C. for 18 hours. The reaction mixture was allowed to cool down to room temperature and was partitioned between ethyl acetate and a saturated solution of sodium bicarbonate. The organic layer was separated, dried over sodium sulfate, filtered and concentrated in vacuo. The residue was purified on silica gel by flash column chromatography to afford the title compound as a colourless oil (160 mg, 76% yield).

Workup

  1. temperatureto cool down to room temperature
  2. customwas partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified on silica gel by flash column chromatography

Sources & evidence

ORD record
ord-075e688788aa4593b4ce4acb05ba18a0
Source dataset
uspto-grants-2012_05
Patent number
US08188071B2

Reaction notes

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