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Potassium Carbonate → 6-Chloro-4-(4-chloro-phenyl)-3-(2,2,2-trifluoro-ethoxy)-pyridazine

HRID 1025948
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HRID 1025948 반응식
Br[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](B(O)O)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.O.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:8][C:6]1[N:5]=[N:4][C:3]([O:9][CH2:10][C:11]([F:14])([F:13])[F:12])=[C:2]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[CH:17][CH:18]=2)[CH:7]=1
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참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 866631334-Bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine

생성물 1

HCID 866631356-Chloro-4-(4-chloro-phenyl)-3-(2,2,2-trifluoro-ethoxy)-pyridazine수율 65.8%

시약·촉매·용매 3

HCID 11979704Tetrakis(triphenylphosphine)palladium
촉매
HCID 962Water용매
HCID 8028Tetrahydrofuran용매

실험 절차

A mixture of 0.676 g 4-bromo-6-chloro-3-(2,2,2-trifluoro-ethoxy)-pyridazine, 363 mg 4-chlorophenylboronic acid, 641 mg potassium carbonate and 134 mg tetrakis(triphenylphosphine) palladium in 15 mL tetrahydrofuran and 15 mL water was heated to reflux for 18 h. The reaction mixture was partitioned between water and ethyl acetate. The phases were separated and the organic phase was purified by chromatography on silica gel using a gradient of heptane:ethyl acetate of 95:5 to 50:50 to yield 0.493 g of the title compound as white solid, MS 323.1 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 18 h
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customThe phases were separated
  5. customthe organic phase was purified by chromatography on silica gel using a gradient of heptane

출처 및 근거

ORD 기록
ord-23efa5f5304d4d71bba9dfcf8a7c9d6e
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08729105B2

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