Hydrochloric Acid → 3-(4-Trifluoromethoxy-phenylamino)-isonicotinic acid

HRID 39602

反応式

HRID 39602 の反応式
F[C:2]1[CH:10]=[N:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:11][C:12]([F:22])([F:21])[O:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[F:11][C:12]([F:21])([F:22])[O:13][C:14]1[CH:15]=[CH:16][C:17]([NH:18][C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 6008484-(Trifluoromethoxy)anilineHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 576496383-(4-Trifluoromethoxy-phenylamino)-isonicotinic acid収率 9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

3-Fluoro-isonicotinic acid (50 mg, 0.354 mmol) and 4-(trifluoromethoxy)aniline (62.8 mg, 0.354 mmol) was added to 2 ml dry THF and the mixture was cooled to −78° C. LiHMDS (1M in THF, 1.24 ml) was added and the mixture was allowed to warm to room temperature over night. Hydrochloric acid (1M in methanol, 5 ml) was added and the volatiles were removed in vacuo. The crude material was purified by preparative HPLC to give 9.5 mg (32 μmol; 9% yield) of pure desired product.

後処理

  1. temperatureto warm to room temperature over night
  2. customthe volatiles were removed in vacuo
  3. customThe crude material was purified by preparative HPLC

出典と根拠

ORDレコード
ord-68aa3eff66cc499abf1b2121278b6d86
出典データセット
uspto-grants-2013_09
特許番号
US08524911B2

関連ノート

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