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

HRID 717553Notes

Reaction equation

HRID 717553 reaction equation
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

Participants

5

Reactant 3

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

Product 1

HCID 178429763HCID 178429763, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4715e5907f8149f5b0df38d63437e244
Source dataset
uspto-grants-2015_11
Patent number
US09193724B2

Reaction notes

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