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Diisopropylamine → Methyl 3-(5-methylpyridin-2-yl)-5-(2-methylpyrimidin-5-yl)benzoate

HRID 888395
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HRID 888395 반응식
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16](B3OC(C)(C)C(C)(C)O3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1.Br[C:28]1[CH:29]=[N:30][C:31]([CH3:34])=[N:32][CH:33]=1.C1C=C(S([O-])(=O)=O)C=C(P(C2C=CC=C(S([O-])(=O)=O)C=2)C2C=CC=C(S([O-])(=O)=O)C=2)C=1.[Na+].[Na+].[Na+].C(NC(C)C)(C)C>CN(C)C=O.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]([CH:15]=[C:16]([C:28]3[CH:29]=[N:30][C:31]([CH3:34])=[N:32][CH:33]=3)[CH:17]=2)[C:11]([O:13][CH3:14])=[O:12])=[N:6][CH:7]=1
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참가 물질

8

반응물 4

HCID 7912DiisopropylamineHCID 6099338Trisodium 3,3',3''-phosphinetriyltris(benzene-1-sulphonate)HCID 143877445-Bromo-2-methylpyrimidineHCID 59432564Methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate

생성물 1

HCID 68496541Methyl 3-(5-methylpyridin-2-yl)-5-(2-methylpyrimidin-5-yl)benzoate수율 65.1%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

To a solution of methyl 3-(5-methylpyridin-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (170 mg, 0.481 mmol) in N,N-dimethylformamide (1.44 mL) and water (0.481 mL) was added 5-bromo-2-methylpyrimidine (167 mg, 0.963 mmol), palladium(II) acetate (5.40 mg, 0.024 mmol), 3,3′3″-phosphinidynetris(benzenesulfonic acid)trisodium salt (41.0 mg, 0.072 mmol) and diisopropylamine (0.171 mL, 1.20 mmol) and the mixture was heated to 80° C. After 1 h, the reaction was allowed to cool to ambient temperature and filtered. Purification by reverse phase chromatography (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid) gave the title compound (100 mg). MS 320.1 (M+1).

후처리

  1. temperatureto cool to ambient temperature
  2. filtrationfiltered
  3. customPurification by reverse phase chromatography (C-18, 95% water/acetonitrile→50% water/acetonitrile with 0.1% trifluoroacetic acid)

출처 및 근거

ORD 기록
ord-638aa800b5844b48889cfc22dd8676ab
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08247401B2

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