Potassium Phosphate, Tribasic → (2-(5-bromo-1((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-phenyl-1H-benzo[d]imidazol-5-yl)methanol

HRID 2068276노트

반응식

HRID 2068276 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2I.[NH2:20][C:21]1[N:25]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:24]2[CH:32]=[CH:33][C:34]([CH2:36][OH:37])=[CH:35][C:23]=2[N:22]=1.CN[C@@H]1CCCC[C@H]1NC.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.C(OCC)(=O)C.[Cu]I>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[N:6]=[C:5]2[NH:20][C:21]1[N:25]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:24]2[CH:32]=[CH:33][C:34]([CH2:36][OH:37])=[CH:35][C:23]=2[N:22]=1

참가 물질

8

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 2733821trans-N,N'-dimethyl-1,2-cyclohexanediamineHCID 21899153(2-amino-1-phenyl-1H-benzo[d]imidazol-5-yl)methanolHCID 583172565-Bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole

생성물 1

HCID 67253458(2-(5-bromo-1((2-(trimethylsilyl)ethoxy)methyl)-1H-indazol-3-ylamino)-1-phenyl-1H-benzo[d]imidazol-5-yl)methanol수율 7.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 5-bromo-3-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (906 mg, 0.00200 mol), (2-amino-1-phenyl-1H-benzoimidazol-5-yl)methanol (435 mg, 0.00182 mol), copper(I) iodide (110 mg, 0.00056 mol), trans-N1,N2-dimethylcyclohexane-1,2-diamine (160 mg, 0.0011 mol) and potassium phosphate (772 mg, 0.00364 mol) in tetrahydrofuran (19.4 mL) was stirred under argon sparging until a greenish suspension formed. The mixture was then microwaved at 140° C. for 3 hours. The reaction mixture was diluted with ethyl acetate and washed with 5% citric acid, saturated sodium bicarbonate, brine, dried over magnesium sulfate and concentrated. The residue was purified by flash chromatography using 0-100% ethyl acetate-hexanes. The product was taken up in ethyl acetate, washed with 1N HCl to remove residual copper and rechromatograped to give 75 mg of product.

후처리

  1. customformed
  2. customThe mixture was then microwaved at 140° C. for 3 hours
  3. washwashed with 5% citric acid, saturated sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography
  7. washwashed with 1N HCl
  8. customto remove residual copper

출처 및 근거

ORD 기록
ord-8ebbd515f52e42528da488b6636751ef
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08293923B2

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