Benzyl Alcohol → Florpyrauxifen-benzyl

HRID 1754134

반응식

HRID 1754134 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

HCID 70495450Florpyrauxifen-benzyl수율 78%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
90 °C

실험 절차

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]+).

후처리

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

출처 및 근거

ORD 기록
ord-6d8c455e4ea0473588dc440192bacff7
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09169217B2

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