Hydrochloric Acid → HCID 67312936, compound

HRID 1908976Notes

Reaction equation

HRID 1908976 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[N:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1(C)C=CC=CC=1.[N:26]1[CH:31]=[C:30]([O:32][C:33]2[CH:38]=[CH:37][N:36]=[C:35]([C:39](OCC3C=CC=CC=3)=[O:40])[CH:34]=2)[CH:29]=[N:28][CH:27]=1.Cl>C1COCC1.CCOC(C)=O>[CH3:8][C:4]1[N:3]=[C:2]([NH:1][C:39](=[O:40])[C:35]2[CH:34]=[C:33]([O:32][C:30]3[CH:29]=[N:28][CH:27]=[N:26][CH:31]=3)[CH:38]=[CH:37][N:36]=2)[CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 157652-Amino-6-methylpyridineHCID 3251421Potassium bis(trimethylsilyl)amideHCID 51038392HCID 51038392, compound

Product 1

HCID 67312936HCID 67312936, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-6-picoline (49 mg, 0.45 mmol, 2.0 eq) was dissolved in THF (0.55 mL) in a flame-dried round bottom flask. A 0.5 M solution of potassium bis(trimethylsilyl)amide in toluene (943 μL, 0.453 mmol, 2.00 eq) was added dropwise and the reaction was stirred for 5 min. Compound 8 (69 mg, 0.22 mmol, 1.0 eq) was added as a solution in THF (0.55 mL) and the reaction was stirred for 30 min. The reaction was diluted with EtOAc, neutralized with 1N HCl and washed with water. The organic layer was dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica gel afforded 45 mg (65%) of the title compound as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 10.32 (s, 1H), 9.19 (s, 1H), 8.92 (s, 2H), 8.69 (d, J=5.6 Hz, 1H), 8.03 (d, J=8.0 Hz, 1H), 7.82-7.75 (m, 1H), 7.71 (d, J=2.5 Hz, 1H), 7.42 (dd, J=5.6, 2.6 Hz, 1H), 7.07 (d, J=7.2 Hz, 1H), 2.43 (s, 3H); [M+1]+: 308.2.

Workup

  1. stirringthe reaction was stirred for 30 min
  2. washwashed with water
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-d085906e56374bccaf0a97a383da78ed
Source dataset
uspto-grants-2013_12
Patent number
US08598345B2

Reaction notes

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