1,2-Dimethoxyethane → HCID 57557271, compound

HRID 1694586Notes

Reaction equation

HRID 1694586 reaction equation
[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][OH:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6](Br)=[CH:5][C:4]=2[N:3]=1.[N:25]1[CH:30]=[CH:29][CH:28]=[C:27](B(O)O)[CH:26]=1.C(=O)([O-])[O-].[K+].[K+].C(COC)OC>C(Cl)(Cl)Cl.CO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[NH2:1][C:2]1[C:11]2[N:12]=[C:13]([CH2:22][OH:23])[N:14]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[C:10]=2[C:9]2[CH:8]=[CH:7][C:6]([C:27]3[CH:26]=[N:25][CH:30]=[CH:29][CH:28]=3)=[CH:5][C:4]=2[N:3]=1

Participants

9

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 67281118[4-amino-7-bromo-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-yl]methanol

Product 1

HCID 57557271HCID 57557271, compoundYield 52.8%

Reagents, catalysts & solvents 4

HCID 178418476HCID 178418476, compoundCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6212ChloroformSolvent2×

Procedure

To a mixture of [4-amino-7-bromo-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-yl]methanol (500 mg, 1.28 mmol), 3-pyridyl boronic acid (233 mg, 1.90 mmol), potassium carbonate (579 mg, 4.20 mmol), dimethoxyethane (5 mL), and water (2.5 mL) under a nitrogen atmosphere was added Pd(PPh3)2Cl2 (18 mg, 0.026 mmol). The resulting suspension was refluxed for 2 hours. The reaction was cooled to ambient temperature. The reaction mixture was diluted with chloroform and placed directly onto a silica gel column. Chromatography (SiO2, 0-40% CMA/CHCl3) gave material that was stirred in methanol and filtered to provide 263 mg of [4-amino-7-pyridin-3-yl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-imidazo[4,5-c]quinolin-2-yl]methanol as tan crystals, m.p. 260-262° C. MS (APCI) m/z 500.3 (M+H)+; Anal. calcd for C22H23N5O2: C, 67.85; H, 5.95; N, 17.98. Found: C, 67.49; H, 5.87; N, 17.83.

Workup

  1. temperatureThe resulting suspension was refluxed for 2 hours
  2. filtrationfiltered

Sources & evidence

ORD record
ord-cb834491d58e4420bddcf39a7ac9fb9c
Source dataset
uspto-grants-2012_04
Patent number
US08158794B2

Reaction notes

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