Water → 4-(7-Bromo-2-methylquinazolin-4-YL)-3-methoxybenzonitrile

HRID 1473679Notes

Reaction equation

HRID 1473679 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1B1OC(C)(C)C(C)(C)O1)[C:6]#[N:7].[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[N:26][C:27]([CH3:31])=[N:28]2)=[CH:23][CH:22]=1.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C(Cl)Cl>[Br:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([C:10]3[CH:9]=[CH:8][C:5]([C:6]#[N:7])=[CH:4][C:3]=3[O:2][CH3:1])=[N:26][C:27]([CH3:31])=[N:28]2)=[CH:23][CH:22]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 222478197-Bromo-4-chloro-2-methylquinazolineHCID 689291003-Methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile

Product 1

HCID 866877614-(7-Bromo-2-methylquinazolin-4-YL)-3-methoxybenzonitrile

Reagents, catalysts & solvents 3

HCID 178418807HCID 178418807, compoundCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of PdCl2(dppf)-CH2Cl2 adduct (0.072 g, 0.088 mmol), 3-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (Intermediate GGGG) (0.500 g, 1.930 mmol), 7-bromo-4-chloro-2-methylquinazoline (0.452 g, 1.754 mmol), and potassium carbonate (0.970 g, 7.02 mmol) in 3 mL dioxane was treated with 1 mL water and was allowed to stir at room temperature 3 hours. LC/MS showed mostly product, so the reaction mixture was diluted with DCM and washed with water. The aqueous layer was removed and the reaction mixture was concentrated. The crude residue was carried forward to step 2 without purification. (M+H)+=354.0.

Workup

  1. washwashed with water
  2. customThe aqueous layer was removed
  3. concentrationthe reaction mixture was concentrated
  4. customThe crude residue was carried forward to step 2 without purification

Sources & evidence

ORD record
ord-dfb36f21679643629f21d398277fb788
Source dataset
uspto-grants-2015_04
Patent number
US09012443B2

Reaction notes

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