Acetic Acid → HCID 59594573, compound

HRID 2262676Notes

Reaction equation

HRID 2262676 reaction equation
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][C:5]([Br:9])=[CH:4][N:3]=1.[CH3:10][CH2:11][C:12](=O)[CH2:13][CH3:14].CC(O)=O>ClC(Cl)C>[Br:9][C:5]1[CH:6]=[C:7]([NH:8][CH:12]([CH2:13][CH3:14])[CH2:11][CH3:10])[C:2]([NH2:1])=[N:3][CH:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 7288Ethyl ketoneHCID 6911565-Bromopyridine-2,3-diamine

Product 1

HCID 59594573HCID 59594573, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 2,3-diamino-5-bromopyridine (10.0 g, 53.2 mmol, 1.0 equiv) and 3-pentanone (6.18 mL, 58.5 mmol, 1.1 equiv) in dichloroethane (150 mL) was added AcOH (3.0 mL, 53.2 mmol, 1.0 equiv) followed by NaHB(OAc)3 (16.9 g, 79.8 mmol, 1.5 equiv), added as a solid in several portions over ˜5 min. The reaction was allowed to stir overnight. The reaction mixture was then washed with satd. aq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. Purification by silica gel MPLC (10%-40% EtOAc/Hexanes) provided 5-bromo-N3-(pentan-3-yl)pyridine-2,3-diamine as an off white solid (2.0 g, 14%). m/z=240.1 [M+H]+

Workup

  1. additionadded as a solid in several portions over ˜5 min
  2. washThe reaction mixture was then washed with satd
  3. dry with materialaq. NaHCO3 and brine, and the resulting organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel MPLC (10%-40% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-2ba2387560ea442f81e0def9ae08e13b
Source dataset
uspto-grants-2010_12
Patent number
US07851484B2

Reaction notes

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