Bromine → HCID 14761929, compound

HRID 1364370Notes

Reaction equation

HRID 1364370 reaction equation
[CH2:1]([C:8]1[CH:9]=[CH:10][C:11]([NH2:14])=[N:12][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:15]Br>C([O-])(O)=O.[Na+]>[CH2:1]([C:8]1[CH:9]=[C:10]([Br:15])[C:11]([NH2:14])=[N:12][CH:13]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 24408Bromine2×HCID 134300735-Benzylpyridin-2-amine

Product 1

HCID 14761929HCID 14761929, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

To a stirred solution of 5-benzylpyridin-2-amine 2 (6.0 g, 32.3 mmol) in CH2C12 (100 mL) cooled to 0° C. was added bromine (5.1 g, 32.3 mmol) dropwise [Kelly, et al., J. Am. Chem. Soc. 112, 8024-8034 (1990)]. The bromine decolorized immediately and the mixture was left stirring for 30 min. The mixture was shaken with saturated NaHCO3 solution (100 mL), the organic layer was then dried over anhydrous Na2SO4, and distilled off to give a yellow residue which was purified by flash chromatography on silica gel (EtOAc:hexane, 3:7). Yield 7.3 g (86%), white solid, mp 110-111° C. 1H NMR (CDCl3, 500 MHz): δ 3.86 (s, 2H, CH2), 4.88 (bs, 2H, NH2), 7.19-7.35 (m, 5H, Ar—H), 7.50 (d, 1H, CH, J=1.5 Hz), 7.94 (d, 1H, CH, J=1.0 Hz). 13C NMR (CDCl3, 125 MHz): δ 37.7, 104.6, 126.4, 126.4, 128.1, 128.6, 128.6, 128.7, 140.2, 140.8, 146.7, 154.0; HRMS (M+H)+ calcd for C12H13BrN2 263.0184, found 263.0184.

Workup

  1. waitthe mixture was left
  2. dry with materialthe organic layer was then dried over anhydrous Na2SO4
  3. distillationdistilled off
  4. customto give a yellow residue which
  5. customwas purified by flash chromatography on silica gel (EtOAc:hexane, 3:7)

Sources & evidence

ORD record
ord-d20c3645c4734b38b41411f03c412835
Source dataset
uspto-grants-2011_02
Patent number
US07888375B2

Reaction notes

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