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

HRID 1473679ノート

反応式

HRID 1473679 の反応式
[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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418807HCID 178418807、化合物触媒HCID 6344Dichloromethane溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dfb36f21679643629f21d398277fb788
出典データセット
uspto-grants-2015_04
特許番号
US09012443B2

反応ノート

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