p-Toluenesulfonic acid → HCID 59815652, compound

HRID 2117357Notes

Reaction equation

HRID 2117357 reaction equation
[CH:1](OC)(OC)OC.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34]2[C:39]([NH2:40])=[CH:38][C:37]([Br:41])=[CH:36][N:35]=2)=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH2:19]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]2[C:34]3=[N:35][CH:36]=[C:37]([Br:41])[CH:38]=[C:39]3[N:40]=[CH:1]2)=[CH:29][CH:28]=1)[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 9005Trimethyl orthoformateHCID 59815651HCID 59815651, compound

Product 1

HCID 59815652HCID 59815652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trimethyl orthoformate (9.0 mL, 81 mmol) and p-toluenesulphonic acid (384 mg, 2.0 mmol) were added to a solution of N2-[4-(benzyloxy)phenyl]-5-bromopyridine-2,3-diamine (3 g, 8.1 mmol) in dichloromethane (40 mL) and the reaction mixture stirred at rt for 4 h. Next, the precipitated material was collected by filtration, redissolved in CH2Cl2 and the solution washed with 10% NaOH(aq) (200 mL) and brine (200 mL), then dried over MgSO4 and concentrated in vacuo to afford 3-[4-(benzyloxy)phenyl]-6-bromo-3H-imidazo[4,5-b]pyridine. 1H NMR (400 MHz, CDCl3) δ 5.14 (s, 2H), 7.16 (d, J=8.8 Hz, 2H), 7.33-7.47 (m, 5H), 7.58 (d, J=8.8 Hz, 2H), 8.25 (s, 1H), 8.28 (d, J=2 Hz, 2H) and 8.46 (d, J=2 Hz, 2H); MS (ES+): m/z 380 [Br79MH+], 382 [Br81MH+].

Workup

  1. filtrationNext, the precipitated material was collected by filtration
  2. dissolutionredissolved in CH2Cl2
  3. washthe solution washed with 10% NaOH(aq) (200 mL) and brine (200 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-68fc2771fd28475782ff2c3d9d2276ee
Source dataset
uspto-grants-2008_10
Patent number
US07442709B2

Reaction notes

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