2-(Tributylstannyl)pyridine → HCID 22609779, compound

HRID 1936781Notes

Reaction equation

HRID 1936781 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23](Br)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Sn](CCCC)(CCCC)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=1)CCC>O1CCOCC1.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>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:32]4[CH:37]=[CH:36][CH:35]=[CH:34][N:33]=4)[CH:24]=3)[N:19]=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6077842-(Tributylstannyl)pyridineHCID 1569266(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine

Product 1

HCID 22609779HCID 22609779, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

The (4-benzyloxy-phenyl)-(6-bromoquinazolin-4-yl)-amine (200 mg, 0.49 mmol), 2-(tributylstannyl)pyridine (200 mg, 0.53 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (3 ml) and heated at reflux under nitrogen for 9 hr. The cooled reaction mixture was absorbed onto silica and purified by flash column chromatography (silica gel, eluting with an ethyl acetate/iso-hexane gradient). The resulting solid was triturated with iso-hexane/ethyl acetate to give the product (110 mg, 56%) as a pale yellow solid; δH [2H6]-DMSO 9.99 (1H, b, NH), 9.18 (1H, s, 5-H), 8.76 (1H, d, pyridine-H), 8.60 (1H, d, 7-H), 8.54 (1H, s, 2-H), 8.23 (1H, d, pyridine-H), 8.00 (1H, t, pyridine-H), 7.87 (1H, d, 8-H), 7.70 (2H, d, 2′-H, 6′-H), 7.53-7.31 (6H, m, 5×Ph-H, pyridine-H), 7.09 (2H, d, 3′-H, 5′-H), 5.14 (2H, s, CH2); m/z 405 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 9 hr
  3. customThe cooled reaction mixture
  4. customwas absorbed onto silica
  5. custompurified by flash column chromatography (silica gel
  6. washeluting with an ethyl acetate/iso-hexane gradient)
  7. customThe resulting solid was triturated with iso-hexane/ethyl acetate

Sources & evidence

ORD record
ord-4c9c5829901b4781a94b42721de56ddb
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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