(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine → (4-Benzyloxy-phenyl)-(6-[5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)furan-2-yl]quinazolinyl)-amine

HRID 1936770Notes

Reaction equation

HRID 1936770 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2C3C(=CC=C(I)C=3)N=[CH:18][N:17]=2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:27][C:28]12[CH2:35][O:34][C:31]([C:36]3[O:40][C:39]([Sn](CCCC)(CCCC)CCCC)=[CH:38][CH:37]=3)([O:32][CH2:33]1)[O:30][CH2:29]2>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([NH:15][C:16]2[N:17]=[CH:18][C:13]3[C:12](=[CH:11][CH:10]=[C:9]([C:39]4[O:40][C:36]([C:31]56[O:30][CH2:29][C:28]([CH3:27])([CH2:33][O:32]5)[CH2:35][O:34]6)=[CH:37][CH:38]=4)[CH:14]=3)[N:15]=2)=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 21951950(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amineHCID 226097085-(4-Methyl-2,6,7-trioxabicyclo[2,2,2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan

Product 1

HCID 22609729(4-Benzyloxy-phenyl)-(6-[5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)furan-2-yl]quinazolinyl)-amineYield 131.4%

Reagents, catalysts & solvents 2

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

Procedure

(4-Benzyloxy-phenyl)-(6-iodoquinazolin-4-yl)-amine (0.925 g, 2.04 mmol), 5-(4-methyl-2,6,7-trioxabicyclo[2.2.2]oct-1-yl)-2-[tri(n-butyl)stannyl]furan (2.00 g, 4.1 mmol) and bis(triphenylphosphine)palladium (II) chloride (catalytic) were reacted in dry dioxane (25 ml) according to Procedure B. Purification by silica gel chromatography and eluting with 100% EtOAc gave the title compound as a yellow solid (0.700 g, 1.34mmol, 66%); δH [2H6]DMSO 10.0 (1H,s), 8.75 (1H,s), 8.48 (1H,s), 8.12 (1H,d), 7.79 (1H,d), 7.66 (2H,d), 7.30-7.52 (5H,m), 7.03-7.12 (3H,m), 6.64 (1H,d), 5.14 (2H,s), 4.06 (6H,s), 0.85 (3H,s).

Workup

  1. customPurification by silica gel chromatography
  2. washeluting with 100% EtOAc

Sources & evidence

ORD record
ord-c6f370a929be4e93b01eb0d2f902a009
Source dataset
uspto-grants-2002_05
Patent number
US06391874B1

Reaction notes

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