Water → 3-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine

HRID 656955ノート

反応式

HRID 656955 の反応式
FC(F)(F)S(O[C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][CH2:16][C:9]=2[CH:8]=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+].O.CO[CH2:28][CH2:29]OC>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:28]([C:7]1[N:12]=[N:11][C:10]2[O:13][CH2:14][CH2:15][CH2:16][C:9]=2[CH:8]=1)=[CH2:29]

参加物

6

反応物 4

HCID 962WaterHCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 866141506,7-dihydro-5H-pyrano[2,3-c]pyridazin-3-yl trifluoromethanesulfonate

生成物 1

HCID 675268253-ethenyl-6,7-dihydro-5H-pyrano[2,3-c]pyridazine収率 77%

試薬・触媒・溶媒 1

HCID 178418397HCID 178418397、化合物触媒

実験手順

Argon was bubbled for 15 minutes through a solution of 6,7-dihydro-5H-pyrano[2,3-c]pyridazin-3-yl trifluoromethanesulfonate (228 mg, 0.8 mmol) in 1,2-dimethoxyethane (6.5 ml). Tetrakis(triphenylphosphine)palladium(0) (50 mg, 0.0475 mmol) was added and the solution stirred for 20 minutes under argon. The mixture was then treated with potassium carbonate (111 mg, 0.8 mmol), water (1.9 ml) and triethenylboroxin pyridine complex (180 mg, 0.75 mmol). After stirring for 2 hours at 80° C., the mixture was cooled and partitioned between DCM and saturated aqueous sodium bicarbonate solution. Layers were separated and the aqueous was extracted twice with 20% MeOH/DCM. The combined organic solution was dried over magnesium sulfate, evaporated and the residue chromatographed on silica, eluting with ethyl acetate to give the product as a white solid (100 mg, 77%).

後処理

  1. stirringAfter stirring for 2 hours at 80° C.
  2. temperaturethe mixture was cooled
  3. custompartitioned between DCM and saturated aqueous sodium bicarbonate solution
  4. customLayers were separated
  5. extractionthe aqueous was extracted twice with 20% MeOH/DCM
  6. dry with materialThe combined organic solution was dried over magnesium sulfate
  7. customevaporated
  8. customthe residue chromatographed on silica
  9. washeluting with ethyl acetate

出典と根拠

ORDレコード
ord-9b03312b503949f799295c6341ec4c12
出典データセット
uspto-grants-2011_12
特許番号
US08071592B2

反応ノート

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