Potassium Carbonate → 2-(4-Hydroxy-2-methyl-phenyl)-4-isopropyl-thiazole-5-carboxylic acid ethyl ester

HRID 250237

反応式

HRID 250237 の反応式
[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9](Br)=[N:8][C:7]=1[CH:12]([CH3:14])[CH3:13])=[O:5])[CH3:2].[CH3:15][C:16]1[CH:17]=[C:18]([OH:31])[CH:19]=[CH:20][C:21]=1B1OC(C)(C)C(C)(C)O1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O>[CH2:1]([O:3][C:4]([C:6]1[S:10][C:9]([C:21]2[CH:20]=[CH:19][C:18]([OH:31])=[CH:17][C:16]=2[CH3:15])=[N:8][C:7]=1[CH:12]([CH3:14])[CH3:13])=[O:5])[CH3:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 9943530Ethyl 2-bromo-4-isopropylthiazole-5-carboxylateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

生成物 1

HCID 1363439712-(4-Hydroxy-2-methyl-phenyl)-4-isopropyl-thiazole-5-carboxylic acid ethyl ester収率 80%

試薬・触媒・溶媒 1

HCID 218864351,4-Dioxane--water (1/1)溶媒

反応条件

温度
100 °C

実験手順

To a solution of 2-bromo-4-isopropyl-thiazole-5-carboxylic acid ethyl ester (834 mg, 3 mmol), 3-methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenol (1.4 g, 6 mmol) and K2CO3 (828 mg, 6 mmol) in 1,4-dioxane/H2O (30 mL/5 mL) is bubbled nitrogen gas for 10 minutes. To this solution is added tetrakistriphenylphosphine palladium (173 mg, 0.15 mmol). The reaction mixture is stirred at 100° C. overnight. The reaction mixture is concentrated under reduced pressure and the residue is partitioned between EtOAc and 1N HCl. The organic phase is concentrated and purified by column chromatography (gradient: 0 to 15% EtOAc in hexanes) to give the title product (730 mg, 80%). 1H NMR (DMSO-d6) δ 9.99 (s, 1H), 7.68 (d, 1H), 6.68, 6.72 (m, 2H), 4.26 (q, 2H), 3.88 (m, 1H), 2.50 (s, 3H), 1.26 (t, 3H), 1.23 (d, 6H).

後処理

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue is partitioned between EtOAc and 1N HCl
  3. concentrationThe organic phase is concentrated
  4. custompurified by column chromatography (gradient: 0 to 15% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-1e497956815d4af6baa589ccc1cc8d2d
出典データセット
uspto-grants-2011_01
特許番号
US07863302B2

関連ノート

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