Triethylamine → N-(4-Bromoisoquinolin-8-yl)nicotinamide

HRID 1454936Notes

Reaction equation

HRID 1454936 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=1.C(N(CC)CC)C.[NH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[C:23]2[C:28]=1[CH:27]=[N:26][CH:25]=[C:24]2[Br:29]>C1COCC1.CCOC(C)=O>[Br:29][C:24]1[C:23]2[C:28](=[C:19]([NH:18][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][CH:6]=[N:5][CH:4]=3)[CH:20]=[CH:21][CH:22]=2)[CH:27]=[N:26][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 884383-Pyridinecarbonyl chloride, hydrochloride (1:1)HCID 4597724-Bromoisoquinolin-8-amine2×

Product 1

HCID 20580764N-(4-Bromoisoquinolin-8-yl)nicotinamide

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Nicotinoyl chloride hydrochloride (356 mg, 2 mmol) and triethylamine (558 μl, 2 mmol) are added to a solution of 8-amino-4-bromoisoquinoline (intermediate 23.2, 446 mg, 0.90 mmol) in anhydrous THF (25 ml). The reaction mixture is stirred overnight, diluted with AcOEt (200 ml) and washed twice with 1N NaOH (100 ml) and then the organic phase is dried over Na2SO4 and evaporated under vacuum. The residue is purified on silica gel, eluting with AcOEt.

Workup

  1. washwashed twice with 1N NaOH (100 ml)
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customevaporated under vacuum
  4. customThe residue is purified on silica gel
  5. washeluting with AcOEt

Sources & evidence

ORD record
ord-fc6380d33f424aff843c7a9fb354ed08
Source dataset
uspto-grants-2009_01
Patent number
US07482342B2

Reaction notes

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