Toluene → HCID 22147975、化合物

HRID 1823967ノート

反応式

HRID 1823967 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

HCID 22147975HCID 22147975、化合物収率 72.5%

試薬・触媒・溶媒 2

HCID 11979704Tetrakis(triphenylphosphine)palladium触媒HCID 962Water溶媒

実験手順

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]+).

後処理

  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

出典と根拠

ORDレコード
ord-a4145a78ff794ec6b59c21d8583de54f
出典データセット
uspto-grants-2006_05
特許番号
US07041689B2

反応ノート

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