Nitrogen → methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate

HRID 1894772노트

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HRID 1894772 반응식
Br[C:2]1[S:3][C:4]2[CH:10]=[C:9]([CH:11]([N:17]3[CH:21]=[CH:20][N:19]=[CH:18]3)[CH:12]([CH2:15][CH3:16])[CH2:13][CH3:14])[CH:8]=[CH:7][C:5]=2[N:6]=1.[CH3:22][O:23][C:24]([C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].N#N>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.O.COCCOC>[CH2:13]([CH:12]([CH2:15][CH3:16])[CH:11]([C:9]1[CH:8]=[CH:7][C:5]2[N:6]=[C:2]([C:29]3[CH:30]=[CH:31][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:27][CH:28]=3)[S:3][C:4]=2[CH:10]=1)[N:17]1[CH:21]=[CH:20][N:19]=[CH:18]1)[CH3:14]

참가 물질

8

반응물 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 27343694-Methoxycarbonylphenylboronic acidHCID 54759530HCID 54759530, 화합물

생성물 1

HCID 54761530methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

A solution of 2-bromo-6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazole (93 mg, 0.255 mmol), (4-(methoxycarbonyl)phenyl)boronic acid (50.6 mg, 0.281 mmol), tetrakis(triphenylphosphine)palladium (29.5 mg, 0.0255 mmol), potassium carbonate (106 mg, 0.765 mmol), DME (5 mL) and water (0.8 mL) was degassed, filled with N2, and heated to 80° C. for 6 h. The reaction mixture was evaporated. The crude product was purified by column chromatography using 5% MeOH in DCM as eluent to afford to methyl 4-(6-(2-ethyl-1-(1H-imidazol-1-yl)butyl)benzo[d]thiazol-2-yl)benzoate as white solid. MS (ES+): m/z 420.28 (MH+).

후처리

  1. customThe reaction mixture was evaporated
  2. customThe crude product was purified by column chromatography

출처 및 근거

ORD 기록
ord-66d1b5318c8442098698fe83310e962e
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513291B2

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