Toluene → HCID 22147975, 화합물

HRID 1823967노트

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HRID 1823967 반응식
[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9](Br)[N:8]=[CH:7]1)(=[O:5])=[O:4].[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[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.O>[CH3:1][N:2]([CH3:12])[S:3]([N:6]1[CH:10]=[C:9]([C:17]2[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=2)[N:8]=[CH:7]1)(=[O:5])=[O:4]

참가 물질

7

반응물 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 221479874-Bromo-N,N-dimethyl-1H-imidazole-1-sulfonamide

생성물 1

HCID 22147975HCID 22147975, 화합물수율 72.5%

시약·촉매·용매 2

HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 962Water용매

실험 절차

A mixture of the bromide from Step 1 (0.543 g), 4-fluorophenylboronic acid (0.31 g), tetrakis(triphenylphosphine) palladium (0) (0.2 g), 2M aqueous sodium carbonate (2.2 mL) and toluene (10 mL) was refluxed under N2 for 1.5 hours. The mixture was cooled, poured into water (75 mL) and extracted with ethyl actetate (2×25 mL). The extracts were dried over Na2SO4, filtered and concentrated. Flash column chromatography, eluting with 40% ethyl acetate-isohexane, gave 1-(dimethylaminosulfonyl)-4-(4-fluorophenyl)imidazole (0.417 g, 72%) as a yellow solid. MS (ES+) 270 ([MH]+).

후처리

  1. temperaturewas refluxed under N2 for 1.5 hours
  2. temperatureThe mixture was cooled
  3. extractionextracted with ethyl actetate (2×25 mL)
  4. dry with materialThe extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash column chromatography, eluting with 40% ethyl acetate-isohexane

출처 및 근거

ORD 기록
ord-a4145a78ff794ec6b59c21d8583de54f
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07041689B2

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