Sodium hydride → HCID 59624544, compound

HRID 1943422Notes

Reaction equation

HRID 1943422 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[C:12]1[C:13]2[N:14]([C:19]([C:22]([NH:24][C:25]3[CH:30]=[CH:29][N:28]=[CH:27][C:26]=3[F:31])=[O:23])=[CH:20][N:21]=2)[N:15]=[C:16]([Cl:18])[CH:17]=1>C1COCC1.CN(C=O)C>[Br:1][C:2]1[N:7]=[C:6]([NH:8][C:12]2[C:13]3[N:14]([C:19]([C:22]([NH:24][C:25]4[CH:30]=[CH:29][N:28]=[CH:27][C:26]=4[F:31])=[O:23])=[CH:20][N:21]=3)[N:15]=[C:16]([Cl:18])[CH:17]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 3008092-Amino-6-bromopyridineHCID 596244958-Bromo-6-chloro-N-(3-fluoropyridin-4-yl)imidazo[1,2-b]pyridazine-3-carboxamide

Product 1

HCID 59624544HCID 59624544, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 6-bromopyridin-2-amine (1.24 g, 7.17 mmol) in THF (10.00 mL) was added 60% NaH (294 mg, 7.35 mmol). The mixture was stirred for 30 min until cessation H2 evolution. The resulting dark green solution was added by syringe to a suspension of 8A (800 mg, 2.453 mmol) in DMF (10 mL). The reaction mixture was stirred at room temperature overnight, and then added to ice water. The brown solid was collected by filtration and dried under vacuum to give 17A (1.125 g, 89%) MS (m+1)=462. HPLC Peak Rt=3.696 minutes (Chromolith column 4.6×50 mm eluting with 10-90% aqueous methanol over 4 minutes containing 0.1% TFA, 4 mL/min, monitoring at 220 nm).

Workup

  1. stirringThe reaction mixture was stirred at room temperature overnight
  2. filtrationThe brown solid was collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-80b323b785254ae892238fe1c03f15a9
Source dataset
uspto-grants-2013_03
Patent number
US08389527B2

Reaction notes

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