Hydrochloric Acid → 4-Pyridinecarboxylic acid, 3-[(4-methoxyphenyl)amino]-

HRID 39600

反応式

HRID 39600 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].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=1.[Li+].C[Si]([N-][Si](C)(C)C)(C)C.Cl>C1COCC1>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([NH:19][C:2]2[CH:10]=[N:9][CH:8]=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])=[CH:15][CH:14]=1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 7732P-AnisidineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 6184714-Pyridinecarboxylic acid, 3-[(4-methoxyphenyl)amino]-収率 13%

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 p-anisidine (44 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 RP chromatography to give 11 mg (45 μmol; 13% yield) of pure desired product. LC-MS (method V): rt=1.82 min; m/z [M+H]+ 245.

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 RP chromatography

出典と根拠

ORDレコード
ord-cdf9d91d0a3f413cb5c8964d06b2c0c7
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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