Hydrogen Bromide → HCID 23658618, compound

HRID 2241804Notes

Reaction equation

HRID 2241804 reaction equation
C[O:2][C:3]1[CH:20]=[CH:19][C:6]2[N:7]=[C:8]([C:10]3[CH:11]=[CH:12][C:13]([N:16]([CH3:18])[CH3:17])=[N:14][CH:15]=3)[O:9][C:5]=2[CH:4]=1.Br.C(=O)(O)[O-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH3:17][N:16]([CH3:18])[C:13]1[N:14]=[CH:15][C:10]([C:8]2[O:9][C:5]3[CH:4]=[C:3]([OH:2])[CH:20]=[CH:19][C:6]=3[N:7]=2)=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 516892Sodium BicarbonateHCID 24780523HCID 24780523, compound

Product 1

HCID 23658618HCID 23658618, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

5-(6-Methoxy-1,3-benzoxazol-2-yl)-N,N-dimethylpyridin-2-amine (31 mg, 0.12 mmol) was mixed with hydrogen bromide (48% aq., 2 mL) and a crystal of tetrabutylammonium bromide was added. The reaction was run at 120° C. for 5 minutes in a microwave reactor. The reaction mixture was added to sodium bicarbonate (sat. aq.) and the solid was collected. The solid was then dissolved in CH2Cl2/ethyl acetate, dried (MgSO4), filtered and evaporated in vacuo, giving the title compound (6 mg) as a purple solid. 1H NMR (400 MHz, CD3OD) δ ppm 8.83 (d, 1H) 8.17 (dd, 1H) 7.44 (d, 1H) 7.02 (d, 1H) 6.75-6.88 (m, 2H) 3.19 (s, 6H); MS m/z (M+H) 256; (M−H) 254.

Workup

  1. customthe solid was collected
  2. dissolutionThe solid was then dissolved in CH2Cl2/ethyl acetate
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-f78d0bd165cd4cf9825f747c0d83e1fb
Source dataset
uspto-grants-2010_03
Patent number
US07670591B2

Reaction notes

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