Dimethylformamide → HCID 86761038、化合物

HRID 1990839ノート

反応式

HRID 1990839 の反応式
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]

参加物

7

反応物 5

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

生成物 1

HCID 86761038HCID 86761038、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-d98b01d0614c4c4cba5b68e0fb26833c
出典データセット
uspto-grants-2010_01
特許番号
US07645753B2

反応ノート

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