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

HRID 385772ノート

反応式

HRID 385772 の反応式
[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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 63651,1-Dichloroethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f4f9b17f558c4953bed704779e9f12d9
出典データセット
uspto-grants-2013_02
特許番号
US08367706B2

反応ノート

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