Sodium Sulfite → HCID 86731462, compound

HRID 509084Notes

Reaction equation

HRID 509084 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[N:20]=[CH:21]3)=[CH:16][CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:36])C(=O)C1.[O-]S([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:36][C:23]1[C:14]([N:11]2[CH2:12][CH2:13][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9][CH2:10]2)=[CH:15][CH:16]=[C:17]2[C:22]=1[CH:21]=[N:20][C:19]([C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18]2

Participants

5

Reactant 3

HCID 24437Sodium SulfiteHCID 67184N-bromobutanimideHCID 86731459HCID 86731459, compound

Product 1

HCID 86731462HCID 86731462, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound ethyl 7-(4-(tert-butoxycarbonyl)piperazin-1-yl)isoquinoline-3-carboxylate (1.1 g, 2.85 mmol) in DCM (10 mL) was added NBS (508 mg, 2.85 mmol) following by stirring at 0° C. for 1 h. To the reaction mixture was added saturated Na2SO3 (20 ml). The combined organic layers were dried by anhydrous Na2SO4, concentrated in vacuo, and washed by PE to afford ethyl 8-bromo-7-(4-(tert-butoxycarbonyl)piperazin-1-yl)isoquinoline-3-carboxylate as a light yellow solid (900 mg, yield: 70%).

Workup

  1. dry with materialThe combined organic layers were dried by anhydrous Na2SO4
  2. concentrationconcentrated in vacuo
  3. washwashed by PE

Sources & evidence

ORD record
ord-49f3a782c9004c0e8bd43fa1d811c31d
Source dataset
uspto-grants-2015_08
Patent number
US09096549B2

Reaction notes

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