(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → (4-Benzyloxy-phenyl)-(6-furan-2-yl-quinazolin-4-yl)-amine

HRID 2306708Notes

Reaction equation

HRID 2306708 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[O:33][CH:34]=[CH:35][CH:36]=1)CCC>O1CCOCC1.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=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[O:33][CH:34]=[CH:35][CH:36]=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 1569266(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amineHCID 43936882-(Tributylstannyl)furan

Product 1

HCID 22609796(4-Benzyloxy-phenyl)-(6-furan-2-yl-quinazolin-4-yl)-amineYield 99.6%

Reagents, catalysts & solvents 2

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The (4-benzyloxy-phenyl)-(6-bromo-quinazolin-4-yl)-amine (300 mg, 0.74 mmol), 2-(tributylstannyl)furan (290 mg, 0.81 mmol) and bis(triphenylphosphine) palladium(II) chloride (catalytic) were dissolved in dioxane (3.5 ml) and heated at reflux under nitrogen for 2 hr. The cooled reaction mixture was absorbed onto silica and purified by flash column chromatography (silica gel, eluting with 1:1 ethyl acetate/iso-hexane) to give the title product (290 mg, 79%) as a pale yellow solid; δH [2H6]-DMSO 9.94 (1H, b, NH), 8.85 (1H, s, 5-H), 8.53 (1H, s, 2-H), 8.21 (1H, d, 7-H), 7.91 (1H, d, furan-H), 7.81 (1H, d, 8-H), 7.72 (2H, d, 2′-H, 6′-H), 7.57-7.33 (5H, m, 5×Ph-H), 7.16 (1H, d, furan-H), 7.10 (2H, d, 3′-H, 5′-H), 6.72, (1H, dd, furan-4H), 5.17 (2H, s, CH2); m/z 394 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 2 hr
  3. customThe cooled reaction mixture
  4. customwas absorbed onto silica
  5. custompurified by flash column chromatography (silica gel, eluting with 1:1 ethyl acetate/iso-hexane)

Sources & evidence

ORD record
ord-26187b990eee4b8290fc39f22e884c6c
Source dataset
uspto-grants-2004_12
Patent number
US06828320B2

Reaction notes

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