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Potassium Phosphate, Tribasic → (6-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

HRID 908232
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HRID 908232 반응식
[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13](Br)=[CH:12][N:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=[C:10]2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2].[CH:25]1(B(O)O)[CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.C1(C)C=CC=CC=1>[C:1]([O:5][C:6](=[O:24])[NH:7][C:8]1[C:13]([CH:25]2[CH2:27][CH2:26]2)=[CH:12][N:11]2[CH:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:17]=[C:10]2[CH:9]=1)([CH3:4])([CH3:3])[CH3:2]
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참가 물질

9

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 67041813(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester

생성물 1

HCID 67041799(6-Cyclopropyl-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester수율 87.3%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

(6-Bromo-2-phenyl-imidazo[1,2-a]pyridin-7-yl)-carbamic acid tert-butyl ester (Example 67, Step 1-3, 600 mg, 1.54 mmol), cyclopropylboronic acid (265 mg, 3.12 mmol), potassium phosphate (1.64 g), tricyclohexylphosphine (95 mg), and palladium(II) acetate (38 mg) were placed in a round-bottom flask, and the flask was filled with an atmosphere of Argon. Toluene (15 ml) and water (1 ml) were added and the mixture was heated to 100° C. overnight. Upon cooling, the reaction mixture was taken up in ethyl acetate and washed. The organic layers were dried (Na2SO4) and evaporated. The title compound (470 mg, 87%) was isolated from the residue by column chromatography (silica gel, heptane:ethyl acetate=100:0-60:40). MS (m/e)=350.4 [M+H+].

후처리

  1. additionthe flask was filled with an atmosphere of Argon
  2. temperatureUpon cooling
  3. washwashed
  4. dry with materialThe organic layers were dried (Na2SO4)
  5. customevaporated

출처 및 근거

ORD 기록
ord-878e1ccd447f48349adeb0716652d676
출처 데이터셋
uspto-grants-2011_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08017604B2

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