(6-Bromoquinazolin-4-yl)[4-(phenylmethoxy)phenyl]amine → HCID 22609706, compound

HRID 1936784Notes

Reaction equation

HRID 1936784 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:36][CH2:35][CH2:34][CH: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:35]4[O:36][CH2:32][CH2:33][CH:34]=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 14323397Tributyl(2,3-dihydrofuran-5-yl)stannane

Product 1

HCID 22609706HCID 22609706, compoundYield 72.2%

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), 5-(tributylstannyl)-2,3-dihydrofuran (250 mg, 0.70 mmol) and bis(triphenylphosphine)palladium(II) chloride (catalytic) were dissolved in dioxan (10 ml) and heated at reflux under nitrogen for 2 hr (Procedure B). The solvent was removed from the cooled reaction under vacuum, and the residue was suspended in 1:1 iso-hexane/ethyl acetate and filtered. The solvent was removed from the filtrate under vacuum to give the product (140 mg, 72%) as a yellow solid; δH [2H6]-DMSO 9.88 (1H, b, NH), 8.62 (1H, s, 5-H), 8.50 (1H, s, 2-H), 8.05 (1H, d, 7-H), 7.67 (3H, m, 8-H, 2′-H, 6′-H), 7.55-7.29 (5H, m, 5×Ph-H), 7.03 (2H, m, 3′-H, 5′-H), 5.81 (1H, s, 3″-H), 5.12 (2H, s, PhCH2), 4.52 (2H, t, 5″-H2), 2.88 (2H, t, 4″-H2); m/z 396 (M+1)+.

Workup

  1. temperatureheated
  2. temperatureat reflux under nitrogen for 2 hr (Procedure B)
  3. customThe solvent was removed from the cooled reaction under vacuum
  4. filtrationfiltered
  5. customThe solvent was removed from the filtrate under vacuum

Sources & evidence

ORD record
ord-6ca5767eca244da1a667bcacfc21b4a8
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

Loading…