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

HRID 855909
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HRID 855909 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])[C:15]([O:20][CH3:21])=[CH:14][C:13]=3[O:22][CH2:23][O:24][CH3:25])[O:11][C:7]=2[CH:6]=[CH:5][CH:4]=1.[NH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>CC#N>[CH3:21][O:20][C:15]1[C:16]([O:18][CH3:19])=[CH:17][C:12]([C:10]2[O:11][C:7]3[CH:6]=[CH:5][CH:4]=[C:3]([CH2:2][NH:26][CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[C:8]=3[N:9]=2)=[C:13]([O:22][CH2:23][O:24][CH3:25])[CH:14]=1
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참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 195092-PyridinemethanamineHCID 219593354-Bromomethyl-2-(4,5-dimethoxy-2-methoxymethoxyphenyl)benzoxazole

생성물 1

HCID 219593292-(4,5-Dimethoxy-2-methoxymethoxyphenyl)-4-(2-pyridylmethyl)aminomethylbenzoxazole수율 17.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 6 (612 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. Insoluble material was removed by filtration and the filtrate was concentrated in vacuo. Water (20 mL) was added to the residue, which was extracted with ethyl acetate (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 7 as pale yellow oil (112 mg, 17%): 1H-NMR (500 MHz, CDCl3) δ3.56 (s, 3H), 3.95 (s, 3H), 3.97 (s, 3H), 4.02 (s, 2H), 4.30 (s, 2H), 5.27 (s, 2H), 6.85 (s, 1H), 7.15 (dd, 1H, J=7.5, 5.0 Hz), 7.28 (t, 1H, J=7.5 Hz), 7.33 (d, 1H, J=7.5 Hz), 7.42 (d, 1H, J=7.5 Hz), 7.47 (d, 1H, J=7.5 Hz), 7.64 (m, 2H), 8.55 (d, 1H, J=5.0 Hz).

후처리

  1. customInsoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated in vacuo
  3. additionWater (20 mL) was added to the residue, which
  4. extractionwas extracted with ethyl acetate (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-3a7d1efe1e644536b4d5beb576ba9872
출처 데이터셋
uspto-grants-2007_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07262301B1

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