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

HRID 250237

반응식

HRID 250237 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

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

반응 조건

온도
100 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1e497956815d4af6baa589ccc1cc8d2d
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07863302B2

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