Methylamine → HCID 68209711, compound

HRID 1406287Notes

Reaction equation

HRID 1406287 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]=O)=[N:6][C:7]=1[O:8][CH3:9].[NH2:12][CH3:13].[BH4-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][NH:12][CH3:13])=[N:6][C:7]=1[O:8][CH3:9]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 4311764Sodium borohydrideHCID 866580025-Bromo-6-methoxypicolinaldehyde

Product 1

HCID 68209711HCID 68209711, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Bromo-6-methoxypicolinaldehyde of preparation 78 (69 mg, 0.32 mmol) in a solution of NH2CH3 in THF (2M, 3 mL) was stirred under nitrogen at room temperature for 45 mins, and LCMS showed a mass of 230 which indicated the presence of the iminium ion. Sodium borohydride (36.2 mg, 0.957 mmol) was added, and the reaction was stirred at room temperature overnight. The desired product was detected by LCMS, and the reaction was quenched with MeOH (0.5 mL) and water (10 ml), then partitioned with EtOAc (10 mL). The organic layer was dried over sodium sulfate, filtered and evaporated to give the title compound as a yellow oil (47 mg), which was taken into the next step without further purification.

Workup

  1. stirringthe reaction was stirred at room temperature overnight

Sources & evidence

ORD record
ord-8e80aa13b2f14a21a147c1de92fe4846
Source dataset
uspto-grants-2014_12
Patent number
US08916593B2

Reaction notes

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