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Methanol → C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine

HRID 420493
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HRID 420493 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:18]#[N:19])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1.B.C1COCC1.CO>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([CH2:18][NH2:19])=[CH:11][C:12]2[N:13]([CH:15]=[CH:16][N:17]=2)[CH:14]=1
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참가 물질

5

반응물 3

HCID 887MethanolHCID 2723981Borane;tetrahydrofuranHCID 666590596-(2,4-Dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile

생성물 1

HCID 24849505C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine수율 102.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
40 °C

실험 절차

In a sealed flask, a solution of 6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (750 mg, 2.6 mmol) in THF (20 mL) was cautiously added to well stirred BH3.THF complex (1.0 M solution in THF, 13 mL, 13.0 mmol) at 0° C. The reaction mixture was heated at 40° C. for 1 h and cooled to RT. MeOH (large excess) and Amberlyst 15 (35 g) were successively added and the resulting mixture was shaken at RT for 30 min. The resin was filtered, washed with MeOH (500 mL), and the desired compound was released with ammonia (1.0 M solution in MeOH, 1.2 L). The NH3-MeOH fraction was evaporated to yield the crude C-[6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridin-7-yl]-methylamine (778 mg) as a yellow oil.

후처리

  1. temperaturecooled to RT
  2. filtrationThe resin was filtered
  3. washwashed with MeOH (500 mL)
  4. customThe NH3-MeOH fraction was evaporated

출처 및 근거

ORD 기록
ord-503c9e429f1e49e5835cebdf280afe2b
출처 데이터셋
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08097617B2

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