Sodium Carbonate → HCID 21959314, compound

HRID 855925Notes

Reaction equation

HRID 855925 reaction equation
Br[CH2:2][C:3]1[C:8]2[N:9]=[C:10]([C:12]3[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:13]=3[O:20][CH2:21][O:22][CH3:23])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[NH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[CH3:19][O:18][C:16]1[CH:15]=[CH:14][C:13]([O:20][CH2:21][O:22][CH3:23])=[C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][NH:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][N:27]=4)[C:8]=3[N:9]=2)[CH:17]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 195092-PyridinemethanamineHCID 219593264-Bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole

Product 1

HCID 21959314HCID 21959314, compoundYield 63.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-bromomethyl-2-(5-methoxy-2-methoxymethoxyphenyl)benzoxazole (F12) (567 mg, 1.5 mmol), 2-(aminomethyl)pyridine (1.08 g, 10 mmol), and Na2CO3 (excess) in CH3CN (30 mL) was stirred overnight at room temperature. After filtration of the reaction mixture, the filtrate was concentrated in vacuo. Water (20 mL) was added to the residue, which was extracted with CHCl3 (20 mL) three times. The combined organic layer was washed with brine and water, dried over MgSO4, and evaporated. The resulting oily material was purified by silica gel column chromatography (CHCl3-ethyl acetate) to afford the objective compound as a pale yellow oil (386 mg, 63%). 1H-NMR (400 MHz, CDCl3) δ3.52 (s, 3H), 3.87 (s, 3H), 4.01 (s, 2H), 4.30 (s, 2H), 5.23 (s, 2H), 7.02 (dd, 1H, J=9.2, 1.2 Hz), 7.15 (dd, 1H, J=7.6, 4.4 Hz), 7.21 (d, 1H, J=9.2 Hz), 7.29-7.36 (m, 2H), 7.41 (d, 1H, J=7.6 Hz), 7.49 (d, 1H, J=7.6 Hz), 7.62-7.65 (m, 2H), 8.55 (d, 1H, J=4.4 Hz).

Workup

  1. filtrationAfter filtration of the reaction mixture
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater (20 mL) was added to the residue, which
  4. extractionwas extracted with CHCl3 (20 mL) three times
  5. washThe combined organic layer was washed with brine and water
  6. dry with materialdried over MgSO4
  7. customevaporated
  8. customThe resulting oily material was purified by silica gel column chromatography (CHCl3-ethyl acetate)

Sources & evidence

ORD record
ord-a417e1565d1744c6b99d707e98d78cb5
Source dataset
uspto-grants-2007_08
Patent number
US07262301B1

Reaction notes

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