Sodium Carbonate → 1-(6-Bromopyridin-2-yl)-N-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]methanamine

HRID 385772노트

반응식

HRID 385772 반응식
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH:10]([C:13]1[N:17]=[C:16]([CH2:18][NH2:19])[O:15][N:14]=1)([CH3:12])[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:19][CH2:18][C:16]2[O:15][N:14]=[C:13]([CH:10]([CH3:12])[CH3:11])[N:17]=2)[CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 5

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 280631563-(1-Methylethyl)-1,2,4-oxadiazole-5-methanamine

생성물 1

HCID 595257901-(6-Bromopyridin-2-yl)-N-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]methanamine

시약·촉매·용매 2

HCID 63651,1-Dichloroethane용매HCID 8857Ethyl Acetate용매

실험 절차

6-Bromopyridine-2-carbaldehyde (1.18 g, 6.34 mmol) and 1-(3-isopropyl-1,2,4-oxadiazol-5-yl)methanamine (0.90 g, 6.34 mmol) were combined and dissolved in dichloroethane (26.0 ml), reacted for 45 minutes, at which time sodium triacetoxyborohydride (1.88 g, 8.88 mmol) was added and the reaction was maintained at room temperature overnight. The reaction was diluted with ethyl acetate followed by the addition of saturated sodium bicarbonate and saturated sodium carbonate to make sure the pH was basic. The organic layer was separated and washed with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude reaction mixture was purified by silica gel chromatography to yield the title compound.

후처리

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction mixture
  8. customwas purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-f4f9b17f558c4953bed704779e9f12d9
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367706B2

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