Dimethylamine → HCID 57803393, compound

HRID 2103356Notes

Reaction equation

HRID 2103356 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 oil was obtained (47% yield), MS: (M+H)+ 214.0, 216.0.

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-dd45b592029846b682dc3455c1bb8e2a
Source dataset
uspto-grants-2009_08
Patent number
US07576089B2

Reaction notes

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