Potassium Phosphate, Tribasic → HCID 53373964、化合物

HRID 335819ノート

反応式

HRID 335819 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]2[O:8][C:9]3[C:14]([C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]=2[CH:3]=1)=[CH:13][C:12]([C:21]1[C:22]([F:28])=[N:23][CH:24]=[CH:25][C:26]=1[F:27])=[CH:11][CH:10]=3.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[O:37]1[CH2:42][CH:41]=[C:40](B2OC(C)(C)C(C)(C)O2)[CH2:39][CH2:38]1>O1CCOCC1.O.CCOC(C)=O.C([O-])([O-])=O.[Na+].[Na+]>[F:28][C:22]1[C:21]([C:12]2[CH:13]=[C:14]3[C@@:15]4([CH2:19][O:18][C:17]([NH2:20])=[N:16]4)[C:4]4[CH:3]=[C:2]([C:40]5[CH2:41][CH2:42][O:37][CH2:38][CH:39]=5)[N:7]=[CH:6][C:5]=4[O:8][C:9]3=[CH:10][CH:11]=2)=[C:26]([F:27])[CH:25]=[CH:24][N:23]=1

参加物

8

反応物 3

HCID 62657Potassium Phosphate, TribasicHCID 112180533,6-Dihydro-2H-pyran-4-boronic acid pinacol esterHCID 86658465HCID 86658465、化合物

生成物 1

HCID 53373964HCID 53373964、化合物

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 10340Sodium Carbonate溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

A glass microwave reaction vessel was charged with (S)-3-chloro-7-(2,4-difluoropyridin-3-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.190 g, 0.474 mmol), potassium phosphate (0.302 g, 1.422 mmol), 2-(3,6-dihydro-2H-pyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (0.169 g, 0.806 mmol) and bis(di-tert-butylphenylphosphine)dichloropalladium (II) (0.029 g, 0.047 mmol) in dioxane (4 mL) and water (1.2 mL). The reaction mixture was heated in microwave at 110° C. for 30 min. The mixture was diluted with EtOAc and saturated Na2CO3. The organic layer was washed twice with saturated Na2CO3, dried over Na2SO4 and concentrated in vacuo. The crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2) to provide a residue that was purified by HPLC to provide the titled compound as a white solid. MS m/z=449.2 [M+H]+. Calculated for C24H18F2N4O3: 448.13.

後処理

  1. customA glass microwave reaction vessel
  2. washThe organic layer was washed twice with saturated Na2CO3
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude residue was purified by silica gel chromatography (2-10% MeOH—CH2Cl2)
  6. customto provide a residue that
  7. customwas purified by HPLC

出典と根拠

ORDレコード
ord-a537a04d38724a61b78054efa7f426f0
出典データセット
uspto-grants-2014_11
特許番号
US08883782B2

反応ノート

読み込み中…