2-Amino-5-fluoropyridine → HCID 69937644, compound

HRID 2401502Notes

Reaction equation

HRID 2401502 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:19]([C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:33]=[N:34][CH:35]=[N:36][CH:37]=2)[CH:30]=1)[C:24](OC)=[O:25])#[N:20]>C1COCC1>[C:19]([C:21]1[CH:22]=[C:23]([CH:28]=[C:29]([O:31][C:32]2[CH:37]=[N:36][CH:35]=[N:34][CH:33]=2)[CH:30]=1)[C:24]([NH:8][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)=[O:25])#[N:20]

Participants

5

Reactant 3

HCID 27377012-Amino-5-fluoropyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 58318794HCID 58318794, compound

Product 1

HCID 69937644HCID 69937644, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

5-fluoropyridin-2-amine (4.2 mg, 0.037 mmol, 1.2 eq) was dissolved in THF (0.20 mL), and potassium bis(trimethylsilyl)amide (13 mg, 0.066 mmol, 2.1 eq) was added. The reaction was stirred at rt for 5 minutes. Compound 9 (8.0 mg, 0.031 mmol, 1.0 eq) was dissolved in THF (0.20 mL) and added to the reaction mixture. The reaction was stirred at rt for 30 minutes, dried on air concentrator, and purified by reverse-phase preparatory HPLC to afford 0.7 mg (10%) of the title compound as a mono-TFA salt: 1H NMR (400 MHz, DMSO-d6) δ 9.10 (s, 1H), 8.78 (s, 2H), 8.41 (d, J=3.0, 1H), 8.27 (t, J=1.3 Hz, 1H), 8.19 (dd, J=9.2, 4.1 Hz, 1H), 8.03-8.00 (m, 2H), 7.81 (td, J=8.7, 3.0 Hz, 1H); ES-MS [M+1]+:336.1.

Workup

  1. additionadded to the reaction mixture
  2. stirringThe reaction was stirred at rt for 30 minutes
  3. customdried on air concentrator
  4. custompurified by reverse-phase preparatory HPLC

Sources & evidence

ORD record
ord-524d7c18c6d140ef915debd0f2d5f4dc
Source dataset
uspto-grants-2014_08
Patent number
US08796295B2

Reaction notes

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