Water → HCID 86700381、化合物

HRID 879557ノート

反応式

HRID 879557 の反応式
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7](B(O)O)=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Br[C:15]1[N:16]([CH3:21])[CH:17]=[C:18]([Br:20])[N:19]=1.O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:20][C:18]1[N:19]=[C:15]([C:7]2[CH:6]=[C:5]3[C:10](=[CH:9][CH:8]=2)[N:2]([CH3:1])[N:3]=[CH:4]3)[N:16]([CH3:21])[CH:17]=1

参加物

7

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 72048802,4-Dibromo-1-methyl-1H-imidazoleHCID 225589101-Methyl-1H-indazole-5-boronic acid

生成物 1

HCID 86700381HCID 86700381、化合物

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
110 °C

実験手順

In a 10-20 mL reaction vial, the 1-methyl-1H-indazol-5-ylboronic acid (169 mg, 0.966 mmol) and the 2,4-dibromo-1-methyl-1H-imidazole (300 mg, 1.25 mmol) were dissolved in dioxane (4 mL) and water (1 mL) under argon atmosphere. The mixture was bubbled with argon for 5 min and then potassium carbonate (400 mg, 2.895 mmol) and Pd(PPh3)4 (167 mg, 0.145 mmol) were added sequentially. The resulting reaction mixture was then sealed and heated in oil bath at 110° C. for 1.5 h. Reaction was then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase was washed with water (3×20 mL) and was concentrated. Residue was purified on silica gel column with 0-50% EtOAc/Hex to afford the desired product. LCMS-ESI+: calc'd for: C12H11BrN4: 291.0, 293.0 (M+H+); found: 291.0, 293.0 (M+H+)

後処理

  1. customIn a 10-20 mL reaction vial
  2. customThe mixture was bubbled with argon for 5 min
  3. customThe resulting reaction mixture
  4. customwas then sealed
  5. customReaction
  6. customwas then partitioned between EtOAc (30 mL) and water (30 mL).The organic phase
  7. washwas washed with water (3×20 mL)
  8. concentrationwas concentrated
  9. customResidue was purified on silica gel column with 0-50% EtOAc/Hex

出典と根拠

ORDレコード
ord-220659e478524ecf93c4d01863e9485b
出典データセット
uspto-grants-2015_03
特許番号
US08987250B2

反応ノート

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