Potassium Carbonate → 5-(4-methoxypyrimidin-2-yl)-1-methyl-1H-indazole

HRID 510322노트

반응식

HRID 510322 반응식
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][N:3]=1.[CH3:10][N:11]1[C:19]2[C:14](=[CH:15][C:16](B(O)O)=[CH:17][CH:18]=2)[CH:13]=[N:12]1.C([O-])([O-])=O.[K+].[K+]>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>[CH3:9][O:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([C:16]2[CH:15]=[C:14]3[C:19](=[CH:18][CH:17]=2)[N:11]([CH3:10])[N:12]=[CH:13]3)[N:7]=1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 5889352-Chloro-4-methoxypyrimidineHCID 225589101-Methyl-1H-indazole-5-boronic acid

생성물 1

HCID 866998545-(4-methoxypyrimidin-2-yl)-1-methyl-1H-indazole

시약·촉매·용매 1

HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
185 °C

실험 절차

2-chloro-4-methoxypyrimidine (100.0 mg, 0.69 mmol), 1-methyl-1H-indazol-5-ylboronic acid (133.9 mg, 0.76 mmol), Pd(PPh3)4 (79.9 mg, 0.069 mmol), and K2CO3 (286.8 mg, 2.075 mmol) were taken in a microwave vial and the vial was vacuum pumped and flushed with argon three times. To this mixture was added degassed toluene (2.5 mL) and DMF (0.28 mL). The reaction mixture was heated in a microwave at 185° C. for 30 min, diluted with ethyl acetate, filtered through Celite (ethyl acetate eluent), and concentrated. Purification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent) provided the product. 1H NMR (400 MHz, CDCl3) δ 8.92 (s, 1H), 8.56 (dd, J=8.9, 1.3 Hz, 1H), 8.52 (d, J=5.8 Hz, 1H), 8.10 (s, 1H), 7.47 (d, J=8.9 Hz, 1H), 6.64 (d, J=5.8 Hz, 1H), 4.14 (s, 3H), 4.12 (s, 3H). LCMS-ESI+: calc'd for C13H13N4O: 241.1 (M+H+); Found: 241.2 (M+H+).

후처리

  1. customflushed with argon three times
  2. additionTo this mixture was added
  3. customdegassed toluene (2.5 mL) and DMF (0.28 mL)
  4. additiondiluted with ethyl acetate
  5. filtrationfiltered through Celite (ethyl acetate eluent)
  6. concentrationconcentrated
  7. customPurification by flash column chromatography on silica gel (hexanes/ethyl acetate eluent)
  8. customprovided the product

출처 및 근거

ORD 기록
ord-192c27a7d74249c4ada67dcff7654062
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096586B2

반응 노트

불러오는 중…