Dimethylformamide → 3-Bromoquinoline-2-carbaldehyde

HRID 389281Notes

Reaction equation

HRID 389281 reaction equation
CC1(C)CCCC(C)(C)N1.[Br:11][C:12]1[CH:13]=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2.CN([CH:25]=[O:26])C>C1COCC1>[Br:11][C:12]1[C:13]([CH:25]=[O:26])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[CH:17][CH:16]=2

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 130352,2,6,6-TetramethylpiperidineHCID 214133-Bromoquinoline

Product 1

HCID 573555563-Bromoquinoline-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To isopropylmagnesium chloride lithium chloride complex solution (1.3M in THF; 50 mL, 65 mmol) was added 2,2,6,6-tetramethylpiperidine (11.5 mL, 68.3 mmol) dropwise, and the mixture was stirred overnight at room temperature. To 55 mL of the resulting solution at −25° C. under N2 was added 3-bromoquinoline (6.52 mL, 48 mmol) dropwise, and the reaction was stirred for 1 hour. DMF (3 mL) was added, and the reaction was slowly warmed to room temperature and monitored by analytical LCMS. The mixture was quenched with saturated aqueous NH4Cl and worked-up. The residue was purified by silica gel chromatography to give the title compound.

Workup

  1. stirringthe reaction was stirred for 1 hour
  2. temperaturethe reaction was slowly warmed to room temperature
  3. customThe mixture was quenched with saturated aqueous NH4Cl
  4. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-8977e22ea4e84de89bac11b74a0109cb
Source dataset
uspto-grants-2013_02
Patent number
US08378107B2

Reaction notes

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