3-Fluorobenzyl bromide → 3-[2-(3-fluorophenyl)ethyl]-N(1,1-dimethylethyl)-2-pyridine carboxamide

HRID 542752

반응식

HRID 542752 반응식
[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].C([Li])CCC.[Br-].[Na+].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br>O1CCCC1.O>[F:22][C:23]1[CH:24]=[C:25]([CH2:26][CH2:14][C:13]2[C:8]([C:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])=[O:7])=[N:9][CH:10]=[CH:11][CH:12]=2)[CH:28]=[CH:29][CH:30]=1

참가 물질

7

반응물 4

HCID 680073-Fluorobenzyl bromideHCID 253881Sodium BromideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium2회

생성물 1

HCID 147168133-[2-(3-fluorophenyl)ethyl]-N(1,1-dimethylethyl)-2-pyridine carboxamide

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-40 °C

실험 절차

Tetrahydrofuran (125 mL) and N-(1,1-dimethylethyl)-3-methyl-2-pyridine carboxamide (1 equivalent) are charged and cooled to -40° C. under nitrogen. Two equivalents of n-butyllithium are then added over 40 minutes. When half the n-butyllithium is added the mixture turns purple. Sodium bromide (1.3 g) is added and then 3-fluoro-benzyl bromide (1.05 equivalents) is added dropwise (1:1 solution in tetrahydrofuran) over 40-50 minutes while the temperature is maintained at -40° C. After 30 minutes at -40° C., the mixture is diluted with water (250 mL) and the organic phase separated. This phase is dried over sodium sulphate and the solvent removed yielding an oil from which solid product, 3-[2-(3-fluorophenyl)ethyl]-N-(1,1-dimethylethyl)-2-pyridine carboxamide, may crystallize.

후처리

  1. temperatureis maintained at -40° C
  2. customthe organic phase separated
  3. dry with materialThis phase is dried over sodium sulphate
  4. customthe solvent removed

출처 및 근거

ORD 기록
ord-92f06b2ab2404965b5290ae9ec535490
출처 데이터셋
uspto-grants-1987_04
특허 번호
US04659716

연결된 노트

불러오는 중…