Water → HCID 57481178, compound

HRID 2167485Notes

Reaction equation

HRID 2167485 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[O:8][CH:9]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]([OH:21])([CH3:20])[CH3:19])=[N:16][CH:17]=2)[N:11]=1.C1C(=O)N([Br:29])C(=O)C1.O>C(Cl)Cl>[Br:29][C:9]1[O:8][C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)=[N:11][C:10]=1[C:12]1[CH:13]=[CH:14][C:15]([C:18]([OH:21])([CH3:19])[CH3:20])=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 58119301HCID 58119301, compound

Product 1

HCID 57481178HCID 57481178, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[5-(2-pyridin-2-yl-1,3-oxazol-4-yl)pyridin-2-yl]propan-2-ol from Step D (75 mg, 0.267 mmol) in DCM (1 mL) was added NBS (62 mg, 0.347 mmol). The reaction mixture was stirred at rt for 16 h. Water was added and the mixture extracted with DCM. The organics were dried (MgSO4), and concentrated to afford 2-[5-(5-bromo-2-pyridin-2-yl-1,3-oxazol-4-yl)pyridin-2-yl]propan-2-ol, which was used without further purification LCMS: m/z 360.0 (M+H)+.

Workup

  1. extractionthe mixture extracted with DCM
  2. dry with materialThe organics were dried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-39a2d4dd1e5a41be931e182b12cfda42
Source dataset
uspto-grants-2015_06
Patent number
US09045467B2

Reaction notes

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