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

HRID 401478Notes

Reaction equation

HRID 401478 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-51de5d674c7149e38ae5031426459268
Source dataset
uspto-grants-2014_06
Patent number
US08741931B2

Reaction notes

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