Potassium Carbonate → HCID 60196492, 화합물

HRID 878236

반응식

HRID 878236 반응식
Br[C:2]1[CH:7]=[CH:6][N:5]=[CH:4][C:3]=1[N:8]([CH3:25])[C:9](=[O:24])[C:10]1[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=1.[CH3:26][C:27]1[S:28][C:29](B2OC(C)(C)C(C)(C)O2)=[C:30]([CH3:32])[N:31]=1.C([O-])([O-])=O.[K+].[K+].COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1>CN(C=O)C.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>[CH3:26][C:27]1[S:28][C:29]([C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[N:8]([CH3:25])[C:9](=[O:24])[C:10]2[CH:15]=[C:14]([C:16]([F:19])([F:18])[F:17])[CH:13]=[C:12]([C:20]([F:23])([F:22])[F:21])[CH:11]=2)=[C:30]([CH3:32])[N:31]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 185257002,4-Dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazoleHCID 86670692N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

생성물 1

HCID 60196492HCID 60196492, 화합물수율 7%

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매

반응 조건

온도
80 °C

실험 절차

A mixture of N-(4-bromo-pyridin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide (200 mg, 0.468 mmol, example 25, intermediate a), 2,4-dimethyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3-thiazole (107.4 mg, 0.7 mmol, CAS RN 859833-13-9) and K2CO3 (193.75 mg, 1.4 mmol) in DMF (6 mL), taken in a sealed tube, was degassed well for 30 min with argon. To this mixture was added S-PHOS (50.1 mg, 0.25 mmol, CAS RN 657408-07-6) and Pd(PPh3)4 (54 mg, 0.05 mmol), and degassed again for 15 min. The reaction mixture was heated to 80° C. for 30 min irradiated with microwave. After the completion of reaction, it was cooled to room temperature, filtered through a bed of celite and the residue washed with EtOAc (50 mL). Volatilities were removed in vacuo and the resultant residue was diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (30 mL), dried over anhydrous Na2SO4, filtered, and evaporated. The crude residue was purified by column chromatography over silica gel (30-40% EtOAc in n-hexane) to afford the title compound as a pale yellow solid (15 mg, 7%). MS (ESI): m/z=460.1 [M+H]+.

후처리

  1. customtaken in a sealed tube
  2. customwas degassed well for 30 min with argon
  3. customdegassed again for 15 min
  4. customirradiated with microwave
  5. customAfter the completion of reaction, it
  6. temperaturewas cooled to room temperature
  7. filtrationfiltered through a bed of celite
  8. washthe residue washed with EtOAc (50 mL)
  9. customVolatilities were removed in vacuo
  10. additionthe resultant residue was diluted with water (30 mL)
  11. extractionextracted with EtOAc (2×50 mL)
  12. washThe combined organic layers were washed with brine (30 mL)
  13. dry with materialdried over anhydrous Na2SO4
  14. filtrationfiltered
  15. customevaporated
  16. customThe crude residue was purified by column chromatography over silica gel (30-40% EtOAc in n-hexane)

출처 및 근거

ORD 기록
ord-fbe99437917448a49d7d8235f51211b9
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987307B2

연결된 노트

불러오는 중…