Water → HCID 10131429, compound

HRID 270138Notes

Reaction equation

HRID 270138 reaction equation
[C:1]([C:5]1[NH:9][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:7](I)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:17]1(B(O)O)[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+].O>C1(C)C=CC=CC=1.CCO>[C:1]([C:5]1[NH:9][C:8]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[C:7]([C:19]2[CH:18]=[CH:17][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[CH:20]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 962WaterHCID 2545321-Naphthaleneboronic acidHCID 516892Sodium BicarbonateHCID 178441779HCID 178441779, compound

Product 1

HCID 10131429HCID 10131429, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent

Procedure

In a heavy-walled pressure vessel 4-(2-tert-Butyl-5-iodo-3-H-imidazol-4-yl)-pyridine (100 milligrams (hereinafter “mg”), 0.3 mmol) and tetrakis-triphenylphosphine palladium (0) catalyst was dissolved in toluene (2-3 ml) and argon was bubbled through the solution while the other reagents were added: 1-naphthyl boronic acid (86 mg, 0.5 mmol), solid NaHCO3 (84 mg), water (500 uL), EtOH (500 uL). The vessel was sealed and the reaction heated to 100° overnight. The reaction mixture was partitioned between 5% NaHCO3 and EtOAc and extracted several times with EtOAc. The combined organic layers were washed with brine, dried over MgSO4, filtered, and evaporated. The crude product was chromatographed on silica gel (chromatotron, eluting with 1-4% MeOH/CH2Cl2) to give the title compound as a yellow solid. (58 mg, 59%). mp 218-220°; MS m/e: 328 [M+H]+, 326 [M−H]−; 1H NMR(400 MHz, CDCl3) δ 9.63(br s, 1H), 8.16(app d, J=4.8 Hz, 2H), 7.92(br d, J=8.3 Hz, 2H), 7.64 (br d, 1H), 7.52 (m, 3H), 7.41 (t, J=6 Hz, 1H), 7.29 (br s, 2H), 1.49 (s, 9H).

Workup

  1. customargon was bubbled through the solution while the other reagents
  2. additionwere added
  3. customThe vessel was sealed
  4. temperaturethe reaction heated to 100° overnight
  5. customThe reaction mixture was partitioned between 5% NaHCO3 and EtOAc
  6. extractionextracted several times with EtOAc
  7. washThe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was chromatographed on silica gel (chromatotron, eluting with 1-4% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-9f6a022b36674a16ac1e273d4a1e7dff
Source dataset
uspto-grants-2008_11
Patent number
US07449484B2

Reaction notes

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