Benzyl Alcohol → Florpyrauxifen-benzyl

HRID 333643

反応式

HRID 333643 の反応式
[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([OH:21])=[O:20])[C:3]=1[Cl:22].C(C1NC=CN=1)(C1NC=CN=1)=O.C(=O)=O.[CH2:38](O)[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>O1CCCC1>[NH2:1][C:2]1[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([O:16][CH3:17])[C:10]=2[F:18])[N:5]=[C:4]([C:19]([O:21][CH2:38][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:20])[C:3]=1[Cl:22]

参加物

6

反応物 4

HCID 244Benzyl AlcoholHCID 280Carbon DioxideHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 67420724Florpyrauxifen

生成物 1

HCID 70495450Florpyrauxifen-benzyl収率 78%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
90 °C

実験手順

To a solution of 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methoxyphenyl)-5-fluoropicolinic acid (prepared by the methods described in U.S. Pat. No. 7,314,849 B2; 100 milligrams (mg), 0.29 millimoles (mmol)) in tetrahydrofuran (THF; 1 milliliter (mL)) was added carbonyl diimidazole (51 mg, 0.32 mmol). The reaction mixture was stirred at ambient temperature for 30 minutes (min) when carbon dioxide (CO2) evolution ceased. Benzyl alcohol (62 mg, 0.58 mmol) was added, and the reaction mixture was heated in a benchtop microwave at 90° C. for 20 min The reaction mixture was purified by silica gel chromatography (applied directly to an Isco 40 gram (g) RediSep® column eluting with 0-100% diethyl ether (Et2O) in hexanes) to yield a white solid (147 mg, 78%): mp 132-133° C., 1H NMR (400 MHz, DMSO-d6) δ 7.50-7.33 (m, 6H), 7.29 (dd, J=8.5, 7.1 Hz, 1H), 7.13 (s, 2H), 5.37 (s, 2H), 3.92 (s, 3H); ESIMS m/z 439 ([M+H]+).

後処理

  1. customwas purified by silica gel chromatography (
  2. washeluting with 0-100% diethyl ether (Et2O) in hexanes)

出典と根拠

ORDレコード
ord-5a92b33564584a43b9919e3b9b0ae7be
出典データセット
uspto-grants-2014_11
特許番号
US08883688B2

関連ノート

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