Dimethylamine → HCID 86619738, compound

HRID 1921218Notes

Reaction equation

HRID 1921218 reaction equation
[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[CH2:12]=O.[CH3:14][NH:15][CH3:16]>CC(O)=O>[Br:1][C:2]1[CH:7]=[N:6][C:5]([Cl:8])=[C:4]2[NH:9][CH:10]=[C:11]([CH2:14][N:15]([CH3:12])[CH3:16])[C:3]=12

Participants

5

Reactant 3

HCID 674DimethylamineHCID 712FormaldehydeHCID 110317234-Bromo-7-chloro-1H-pyrrolo(2,3-c)pyridine

Product 1

HCID 86619738HCID 86619738, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-7-chloro-1H-pyrrolo[2,3-c]pyridine (Zhang et al., J. Org. Chem., 2002, 67, 2345-2347) (200 mg, 0.864 mmol), formaldehyde (37 wt. % in H2O, 0.500 mL, 6.17 mmol), and dimethylamine (40 wt. % in H2O, 1.00 mL, 8.88 mmol) in AcOH (6 mL) was heated in a microwave reactor at 100° C. for 40 min. The solvent was removed under reduced pressure. The crude product was partitioned between CH2Cl2 (15 mL) and saturated NaHCO3 (10 mL). The layers were separated and the organic layer was dried over Na2SO4, filtered, and concentrated in vacuo. Purification of the crude product by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH—100:0 to 90:10, gave the title compound. MS: m/z=290 (M+1).

Workup

  1. customThe solvent was removed under reduced pressure
  2. customThe crude product was partitioned between CH2Cl2 (15 mL) and saturated NaHCO3 (10 mL)
  3. customThe layers were separated
  4. dry with materialthe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification of the crude product by silica gel chromatography
  8. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-08f1d43257bb4c239c0c6c37bfaa0f7f
Source dataset
uspto-grants-2012_05
Patent number
US08173655B2

Reaction notes

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