2-Amino-4-chloropyridine → HCID 178429763, 화합물

HRID 717553노트

반응식

HRID 717553 반응식
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

참가 물질

5

반응물 3

HCID 5818662-Amino-4-chloropyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 71743410HCID 71743410, 화합물

생성물 1

HCID 178429763HCID 178429763, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-4715e5907f8149f5b0df38d63437e244
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193724B2

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