Potassium Carbonate → 2-(4-Methoxy-phenyl)-thiazole

HRID 1669507

反応式

HRID 1669507 の反応式
Br[C:2]1[S:3][CH:4]=[CH:5][N:6]=1.[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12](B(O)O)=[CH:11][CH:10]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:2]2[S:3][CH:4]=[CH:5][N:6]=2)=[CH:11][CH:10]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 201262(4-Methoxyphenyl)boronic acid

生成物 1

HCID 112984492-(4-Methoxy-phenyl)-thiazole収率 50%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

実験手順

A mixture of 2-bromothiazole (2.0 g, 12.2 mmol), (4-methoxyphenyl)boronic acid (1.9 g, 12.8 mmol), K2CO3 (5.0 g, 36.5 mmol) and (Ph3P)4Pd (0.7 g, 0.61 mmol) in dioxane (40 mL) was refluxed for 16 h. After the solids were filtered off, the filtrate was concentrated in vacuo. The residue was purified by a column chromatography on silica gel to yield the title compound (1.1 g, 50%). 1HNMR (400 MHz, CDCl3) δ 3.86 (s, 3H), 6.96 (d, J=8.8 Hz, 2H), 7.25 (d, J=3.2 Hz, 1H), 7.81 (d, J=3.2 Hz, 1H), 7.90 (d, J=8.8 Hz, 2H), MS m/z 192 (M+1).

後処理

  1. temperaturewas refluxed for 16 h
  2. filtrationAfter the solids were filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by a column chromatography on silica gel

出典と根拠

ORDレコード
ord-7dcb3fc5b6774c8c97a5eb1a7a548592
出典データセット
uspto-grants-2011_08
特許番号
US07989480B2

関連ノート

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