Pyridine → HCID 57757842, compound

HRID 229360Notes

Reaction equation

HRID 229360 reaction equation
C(NC(NC1[N:8]=[C:9]2[CH:14]=[C:13]([C:15]3[CH:16]=[N:17][C:18](OC)=[N:19][CH:20]=3)[CH:12]=[CH:11][N:10]2C=1)=O)C.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[N:35]1[CH:40]=CC=C[CH:36]=1>C(OCC)(=O)C>[NH2:8][C:9]1[CH:14]=[C:13]([C:15]2[CH:20]=[N:19][C:18]([N:35]([CH3:40])[CH3:36])=[N:17][CH:16]=2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 11404171HCID 11404171, compound

Product 1

HCID 57757842HCID 57757842, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

2-Amino-4-bromopyridine 4 (5.00 g, 28.9 mmol) and p-toluenesulfonyl chloride (6.10 g, 31.8 mmol) were dissolved in dry pyridine (100 mL) and heated at 80° C. for 5 h. The pyridine was removed under reduced pressure to give a solid. The solid was suspended in ethyl acetate, then collected by filtration and washed with ethyl acetate to give the tosylate 5 as a crystalline solid (yield: 7.50 g, 79%); 1H NMR [400 MHz, (CD3)2SO] δ 11.6 (v br s, 1H), 7.99 (br d, J=5.6 Hz, 1H), 7.78 (d, J=8.3 Hz, 2H), 7.37 (d, J=7.0 Hz, 2H), 7.27 (br s, 1H), 7.17 (br d, J=5.2 Hz, 1H), 2.36 (s, 3H).

Workup

  1. customThe pyridine was removed under reduced pressure
  2. customto give a solid
  3. filtrationcollected by filtration
  4. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-75769944181a46bba265b4bd0351a1fe
Source dataset
uspto-grants-2009_07
Patent number
US07563788B2

Reaction notes

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