Water → HCID 86700381, 화합물

HRID 879557노트

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HRID 879557 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

HCID 86700381HCID 86700381, 화합물

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

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+)

후처리

  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

출처 및 근거

ORD 기록
ord-220659e478524ecf93c4d01863e9485b
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987250B2

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