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

HRID 2205616노트

반응식

HRID 2205616 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-86bf7020f3bd40e9b45cd148bf117f47
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09371321B2

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