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

HRID 1669507

반응식

HRID 1669507 반응식
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

참가 물질

6

반응물 3

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

생성물 1

HCID 112984492-(4-Methoxy-phenyl)-thiazole수율 50%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7dcb3fc5b6774c8c97a5eb1a7a548592
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989480B2

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