4-Bromo-2-methylaniline → 3-[(4-Bromo-2-methylphenyl)amino]isonicotinic acid

HRID 39500

반응식

HRID 39500 반응식
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.F[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15]2[CH:14]=[N:13][CH:12]=[CH:11][C:16]=2[C:17]([OH:19])=[O:18])=[C:4]([CH3:9])[CH:3]=1

참가 물질

5

반응물 3

HCID 114234-Bromo-2-methylanilineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

생성물 1

HCID 576496333-[(4-Bromo-2-methylphenyl)amino]isonicotinic acid수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

4-Bromo-2-methylaniline (186 mg, 1.00 mmol) and 3-fluoropyridine-4-carboxylic acid (141 mg, 1.00 mmol) were dissolved in dry THF (6.0 ml) under argon and the mixture was cooled to −78° C. A solution of LiHMDS (1.0M in THF, 3.5 ml) was added and the reaction mixture was allowed to warm to ambient temperature. After 24 h the reaction was quenched by adding a solution of HCl in dioxane (4.0M, 2.0 ml). The volatiles were removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 215 mg (701 μmol; 70% yield) of pure desired product.

후처리

  1. temperatureto warm to ambient temperature
  2. customAfter 24 h the reaction was quenched
  3. additionby adding a solution of HCl in dioxane (4.0M, 2.0 ml)
  4. customThe volatiles were removed in vacuo
  5. customthe crude material was purified by flash chromatography

출처 및 근거

ORD 기록
ord-6ba523ef9dc847a191a1366eee7dff78
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524911B2

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