Lithium diisopropylamide → 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one

HRID 1855295ノート

反応式

HRID 1855295 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:15][C:16]2[C:17]([F:23])=[N:18][C:19]([Cl:22])=[CH:20][CH:21]=2)=[C:6]([CH:14]=1)[C:7](N(CC)CC)=[O:8].C([N-]C(C)C)(C)C.[Li+].CCCCCCC.C1COCC1.C(C1C=CC=CC=1)C>C1COCC1>[Br:1][C:2]1[CH:14]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:15][C:16]1[C:17]([F:23])=[N:18][C:19]([Cl:22])=[CH:20][C:21]=1[C:7]2=[O:8]

参加物

5

反応物 3

HCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzolHCID 86640732HCID 86640732、化合物

生成物 1

HCID 574756427-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 5-bromo-2-(6-chloro-2-fluoropyridin-3-yloxy)-N,N-diethylbenzamide (120 mg, 0.299 mmol) in 5 mL of dry THF at −78° C. was added dropwise lithium diisopropylamide, 2.0M heptane/THF/ethylbenzene (158 μL, 1.195 mmol) (0.6 mL of 2M solution) and the reaction was stirred at −78° C. for 3 h. The reaction was quenched at −78° C. with sat. NH4Cl and was allowed to warm up to RT. The reaction was extracted with ETOAc, dried over Na2SO4, filtered and evaporated to dryness. The crude was purified by column chromatography (1:1 hexane/DCM to 100% DCM) to give the titled compound, 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one, as an offwhite solid. MS (M+1): 328.

後処理

  1. customThe reaction was quenched at −78° C. with sat. NH4Cl
  2. temperatureto warm up to RT
  3. extractionThe reaction was extracted with ETOAc
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe crude was purified by column chromatography (1:1 hexane/DCM to 100% DCM)

出典と根拠

ORDレコード
ord-292ef61033a547029fd7f788d58d8c3a
出典データセット
uspto-grants-2015_02
特許番号
US08962859B2

反応ノート

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