Sodium Carbonate → 2-(5-Methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole

HRID 2213999노트

반응식

HRID 2213999 반응식
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

참가 물질

5

반응물 3

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

생성물 1

HCID 219593142-(5-Methoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole수율 63.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-dc9e49afab9c4e6894f9747730eac9d1
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07105680B1

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