Dimethylamine → HCID 57803393, compound

HRID 1809883Notes

Reaction equation

HRID 1809883 reaction equation
[CH3:1][NH:2][CH3:3].[Br:4][C:5]1[N:10]=[CH:9][C:8]([CH:11]=O)=[CH:7][CH:6]=1.[BH4-].[Na+]>CO.CC(C)[O-].CC(C)[O-].CC(C)[O-].CC(C)[O-].[Ti+4]>[Br:4][C:5]1[N:10]=[CH:9][C:8]([CH2:11][N:2]([CH3:3])[CH3:1])=[CH:7][CH:6]=1

Participants

6

Reactant 3

HCID 674DimethylamineHCID 4311764Sodium borohydrideHCID 117692346-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 57803393HCID 57803393, compoundYield 47%

Reagents, catalysts & solvents 2

HCID 11026Titanium isopropoxideCatalystHCID 887MethanolSolvent2×

Procedure

To a solution of titanium tetraisopropoxide (6.4 g, 22 mmol) and 2.0 M of dimethylamine in methanol (22 mL, 44 mmol), 6-bromo-pyridine-3-carbaldehyde (2.10 g, 11 mmol) in 20 mL of methanol was added. After being stirred at r. t. for 5 hrs, sodium borohydride (0.43 g, 11 mmol) was added and the mixture was stirred overnight. The reaction was quenched by addition of 10 mL of water and extracted twice using EtOAc. The combined extracts were dried and concentrated. After flash column using 20-40% methanol in EtOAc and 0.5% NH4OH, 1.15 g of oil was obtained (47% yield), MS: 214.0, 216.0 (M++1).

Workup

  1. stirringthe mixture was stirred overnight
  2. customThe reaction was quenched by addition of 10 mL of water
  3. extractionextracted twice using EtOAc
  4. customThe combined extracts were dried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1b6463f47298415b8aa220c2f1e31319
Source dataset
uspto-grants-2013_01
Patent number
US08362003B2

Reaction notes

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