2-Amino-4-chloropyridine → HCID 178429763、化合物

HRID 717553ノート

反応式

HRID 717553 の反応式
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH2:18])[CH:13]=1.[CH3:19][C:20]1[C:25]([C:26]#[N:27])=[CH:24][N:23]=[CH:22][C:21]=1[F:28]>O1CCCC1>[Cl:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]([NH:18][C:26]([C:25]2[CH:24]=[N:23][CH:22]=[C:21]([F:28])[C:20]=2[CH3:19])=[NH:27])[CH:13]=1

参加物

5

反応物 3

HCID 5818662-Amino-4-chloropyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 71743410HCID 71743410、化合物

生成物 1

HCID 178429763HCID 178429763、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Potassium bis(trimethylsilyl)amide (1.0 M, 4.1 mL, 0.0041 mol) was added slowly for a period of 5 min to a solution of 4-chloro pyridin-2-amine (0.35 g, 0.00273 mol) in anhydrous tetrahydrofuran (30 mL) at 0° C. and stirred for 15 min at same temperature. Then 4-methyl-5-fluoronicotinonitrile (0.37 g, 0.00273 mol) in tetrahydrofuran (5 mL) was added. The reaction temperature was raised to RT and the reaction mixture was stirred it for 18 h. The reaction mixture was quenched with a saturated aqueous ammonium chloride solution (30 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were dried over sodium sulphate and concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford the title compounds. 1H NMR (400 MHz, CDCl3) δ 10.60 (bs, 1H), 8.53 (s, 1H), 8.43 (s, 1H), 8.25-8.24 (d, J=4 Hz, 1H), 7.25-7.24 (d, J=4 Hz, 1H), 7.02-7.00 (d, J=4 Hz, 1H), 2.48 (s, 3H), MS (M+1): 265.1.

後処理

  1. stirringthe reaction mixture was stirred it for 18 h
  2. customThe reaction mixture was quenched with a saturated aqueous ammonium chloride solution (30 mL)
  3. extractionextracted with ethyl acetate (2×50 mL)
  4. dry with materialThe combined organic layers were dried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customto afford the crude product, which
  7. customwas purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4715e5907f8149f5b0df38d63437e244
出典データセット
uspto-grants-2015_11
特許番号
US09193724B2

反応ノート

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