Dimethylformamide → HCID 86761038, 화합물

HRID 1990839노트

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HRID 1990839 반응식
Br[C:2]1[CH:3]=[C:4](OCC)[C:5]([O:8][CH3:9])=[N:6][CH:7]=1.BrC1N=C(OC)[C:17]([O:22]CC)=[CH:16]C=1.[Li]CCCC.CN([CH:33]=[O:34])C.[Cl-].[NH4+]>C1COCC1>[CH2:17]([O:22][C:7]1[C:2]([CH:33]=[O:34])=[CH:3][CH:4]=[C:5]([O:8][CH3:9])[N:6]=1)[CH3:16]

참가 물질

7

반응물 5

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 666174095-Bromo-3-ethoxy-2-methoxypyridineHCID 86607632Pyridine, 6-bromo-3-ethoxy-2-methoxy-HCID 178418339Butyllithium

생성물 1

HCID 86761038HCID 86761038, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a 3:2 mixture of 5-bromo-3-ethoxy-2-methoxy-pyridine and 6-bromo-3-ethoxy-2-methoxy-pyridine (1.0 g, 4.31 mmol, 1.0 equiv) in anhydrous THF (20 mL) was added at −78° C. under Ar a solution of n-BuLi (3.23 mL, 5.17 mmol, 1.2 equiv, 1.6 M solution in hexane). After stirring for 1 h, anhydrous DMF (0.7 mL, 9.05 mmol, 2.1 equiv) was added and the reaction mixture stirred for an additional 30 min. A sat. solution of ammonium chloride (20 mL) was added and the solution extracted with ethyl acetate (3×50 mL). The combined organic phases were dried over MgSO4, the solvent removed by evaporation under reduced pressure and the crude material purified by twice recrystallization from isopropanol yielding 0.35 g (75%) of the title compound. 1H NMR (300 MHz, CDCl3): δ 1.50 (t, J=7.0 Hz, 3H), 4.11 (s, 3H), 4.15 (q, J=7.0 Hz, 2H), 7.46 (d, J=1.9 Hz, 1H), 8.19 (d, J=1.9 Hz, 1H), 9.93 (s, 1H). 13C NMR (75 MHz, CDCl3): δ 14.44, 54.67, 64.59, 113.72, 127.59, 144.29, 144.31, 158.80, 189.66. MS (ISP): 181.8 [M+H]+.

후처리

  1. stirringthe reaction mixture stirred for an additional 30 min
  2. extractionthe solution extracted with ethyl acetate (3×50 mL)
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent removed by evaporation under reduced pressure
  5. customthe crude material purified by twice recrystallization from isopropanol yielding 0.35 g (75%) of the title compound

출처 및 근거

ORD 기록
ord-d98b01d0614c4c4cba5b68e0fb26833c
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07645753B2

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