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

HRID 1473679노트

반응식

HRID 1473679 반응식
[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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 178418807HCID 178418807, 화합물촉매HCID 6344Dichloromethane용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-dfb36f21679643629f21d398277fb788
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09012443B2

반응 노트

불러오는 중…