Water → 7-Bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline

HRID 1473665ノート

反応式

HRID 1473665 の反応式
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](Cl)=[N:7][C:8]([O:12][CH3:13])=[N:9]2)=[CH:4][CH:3]=1.[CH3:15][O:16][C:17]1[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>O1CCOCC1.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:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:18]3[CH:19]=[CH:20][C:21]([C:23]([F:26])([F:25])[F:24])=[CH:22][C:17]=3[O:16][CH3:15])=[N:7][C:8]([O:12][CH3:13])=[N:9]2)=[CH:4][CH:3]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 24901776(2-Methoxy-4-(trifluoromethyl)phenyl)boronic acidHCID 866877407-Bromo-4-chloro-2-methoxyquinazoline

生成物 1

HCID 866877417-Bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline収率 5.39%

試薬・触媒・溶媒 2

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

実験手順

The crude residue from step 2 was dissolved in 22 mL dioxane and was treated with PdCl2(dppf)-CH2Cl2 adduct (0.608 g, 0.745 mmol), (2-methoxy-4-(trifluoromethyl)phenyl)boronic acid (1.802 g, 8.19 mmol), potassium carbonate (4.12 g, 29.8 mmol), and 8 mL water was added. The reaction mixture was allowed to stir at room temperature overnight. LC/MS showed product, so the aqueous layer was removed, and the reaction mixture was concentrated. Purification of the crude residue by silica gel column chromatography (0-50% EtOAc/heptane) gave 7-bromo-2-methoxy-4-(2-methoxy-4-(trifluoromethyl)phenyl)quinazoline (0.166 g, 0.402 mmol, 5.39% yield). (M+H)+=413.0.

後処理

  1. additionwas added
  2. customso the aqueous layer was removed
  3. concentrationthe reaction mixture was concentrated
  4. customPurification of the crude residue by silica gel column chromatography (0-50% EtOAc/heptane)

出典と根拠

ORDレコード
ord-0e4dd66f39f7463ea3ec55c906f37bc4
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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