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

HRID 2213999ノート

反応式

HRID 2213999 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-dc9e49afab9c4e6894f9747730eac9d1
出典データセット
uspto-grants-2006_09
特許番号
US07105680B1

反応ノート

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