Water → 3-Ethenyl-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine

HRID 15154

반응식

HRID 15154 반응식
Cl[C:2]1[N:7]=[N:6][C:5]2[S:8][CH2:9][CH2:10][O:11][C:4]=2[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].B1(C=C)OB([CH:24]=[CH2:25])OB(C=C)O1.C1C=CN=CC=1.O>C(COC)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:24]([C:2]1[N:7]=[N:6][C:5]2[S:8][CH2:9][CH2:10][O:11][C:4]=2[CH:3]=1)=[CH2:25]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27348062,4,6-Trivinylboroxin-Pyridine ComplexHCID 866230793-Chloro-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine

생성물 1

HCID 675272733-Ethenyl-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine수율 71.2%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

반응 조건

온도
96 °C

실험 절차

A solution of 3-chloro-6,7-dihydro[1,4]oxathiino[3,2-c]pyridazine (450 mg, 2.4 mmol) in dimethoxyethane (12 ml) was treated with tetrakis(triphenylphosphine)palladium (0) (61 mg), potassium carbonate (313 mg), 2,4,6-trivinylcyclotriboroxane pyridine complex (375 mg) and water (1.5 ml). The mixture was heated at 96° C., overnight. The mixture was evaporated to dryness, treated with aqueous sodium bicarbonate solution, extracted (4×) with DCM, dried (sodium sulphate), evaporated and chromatographed on silica gel (50 g), eluting with 1:1 ethyl acetate-hexane, affording a solid (200 mg, 46%), containing slightly impure product.

후처리

  1. customThe mixture was evaporated to dryness
  2. additiontreated with aqueous sodium bicarbonate solution
  3. extractionextracted (4×) with DCM
  4. dry with materialdried (sodium sulphate)
  5. customevaporated
  6. customchromatographed on silica gel (50 g)
  7. washeluting with 1:1 ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-ddbc66b9b4ed49d5bcddcc05649432f6
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732460B2

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