Sodium borohydride → 1-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)propan-1-amine

HRID 2205616ノート

反応式

HRID 2205616 の反応式
[CH2:1]([Mg]Br)[CH3:2].[Br:5][C:6]1[CH:7]=[C:8]2[N:16]([CH3:17])[CH:15]=[CH:14][C:9]2=[N:10][C:11]=1[C:12]#[N:13].[BH4-].[Na+]>C1COCC1>[Br:5][C:6]1[CH:7]=[C:8]2[N:16]([CH3:17])[CH:15]=[CH:14][C:9]2=[N:10][C:11]=1[CH:12]([NH2:13])[CH2:1][CH3:2]

参加物

5

反応物 3

HCID 4311764Sodium borohydrideHCID 867079636-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrileHCID 178418443HCID 178418443、化合物

生成物 1

HCID 1182077581-(6-Bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)propan-1-amine収率 81%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

Ethylmagnesium bromide (4.18 mL, 12.54 mmol) was added to a stirred solution of 6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile (740 mg, 3.13 mmol) in THF (16 mL) at room temperature. The mixture was stirred for one hour at room temperature and then quenched with methanol (5 mL). Sodium borohydride (237 mg, 6.27 mmol) was added. The reaction mixture was stirred for one hour, quenched with 1N HCl (1.5 mL) and stirred for 20 minutes. Next, the mixture was basified with saturated aqueous sodium bicarbonate and extracted with ethyl acetate (2×). The organic layer was dried over anhydrous magnesium sulfate and concentrated to give the title compound as a tan oil (680 mg, 81%). ESI-MS m/z [M+H]+ calc'd for C11H14BrN3, 268. found 268.

後処理

  1. customquenched with methanol (5 mL)
  2. stirringThe reaction mixture was stirred for one hour
  3. customquenched with 1N HCl (1.5 mL)
  4. stirringstirred for 20 minutes
  5. extractionextracted with ethyl acetate (2×)
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-86bf7020f3bd40e9b45cd148bf117f47
出典データセット
uspto-grants-2016_06
特許番号
US09371321B2

反応ノート

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