Dimethylformamide → HCID 68673093, compound

HRID 445701Notes

Reaction equation

HRID 445701 reaction equation
NC1[C:3]([F:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.IC.[CH3:12][N:13]([CH:15]=O)[CH3:14]>[H-].[Na+].CCOC(C)=O>[Br:8][C:6]1[CH:7]=[C:15]([N:13]([CH3:14])[CH3:12])[C:3]([F:9])=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 177501445-Bromo-2-fluoropyridin-3-amine

Product 1

HCID 68673093HCID 68673093, compound

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 24758Sodium hydrideSolvent

Procedure

A mixture of 3-amino-5-bromo-2-fluoropyridine (Matrix Scientific, Columbia, S.C., USA, 1.571 mmol) in DMF (3 ml) and 55% NaH in oil (1.571 mmol) was stirred for 15 min at rt. Was added iodomethane (Aldrich, Buchs, Switzerland, 1.571 mmol) and the RM was stirred for 13 h at rt. The RM was diluted with EtOAc, washed with brine (4×), dried over Na2SO4, filtered and evaporated. The residue was absorbed on silica gel and purified by flash chromatography (heptane/EtOAc 0% to 40%). The fraction containing the first eluting product were evaporated to give (5-bromo-2-fluoro-pyridin-3-yl)-dimethyl-amine as an orange oil (HPLC: tR 3.15 min (Method A); M+H=219, 221 MS-ES) and the fraction containing the second eluting product were evaporated to give the title compound as a red solid (HPLC: tR 2.90 min (Method A); M+H=205, 207 MS-ES).

Workup

  1. stirringthe RM was stirred for 13 h at rt
  2. washwashed with brine (4×)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was absorbed on silica gel
  7. custompurified by flash chromatography (heptane/EtOAc 0% to 40%)
  8. additionThe fraction containing the first eluting product
  9. customwere evaporated

Sources & evidence

ORD record
ord-b18e7adbfe364a0ab9d62505f99c0fc8
Source dataset
uspto-grants-2013_07
Patent number
US08476294B2

Reaction notes

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