Sodium Carbonate → N-(4-{(E)-2-[3-tert-butyl-5-(2,6-dimethoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-3-methoxymethyl-phenyl) methanesulfonamide

HRID 2390856노트

반응식

HRID 2390856 반응식
Br[C:2]1[CH:3]=[C:4]([C:26]([CH3:29])([CH3:28])[CH3:27])[C:5]([O:24][CH3:25])=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:19])=[O:18])=[CH:12][C:11]=2[CH2:21][O:22][CH3:23])[CH:7]=1.[CH3:30][O:31][C:32]1[C:37](B(O)O)=[CH:36][CH:35]=[C:34]([O:41][CH3:42])[N:33]=1.C([O-])([O-])=O.[Na+].[Na+]>CO.C(Cl)Cl.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>[C:26]([C:4]1[C:5]([O:24][CH3:25])=[C:6](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([NH:16][S:17]([CH3:20])(=[O:18])=[O:19])=[CH:12][C:11]=2[CH2:21][O:22][CH3:23])[CH:7]=[C:2]([C:37]2[C:32]([O:31][CH3:30])=[N:33][C:34]([O:41][CH3:42])=[CH:35][CH:36]=2)[CH:3]=1)([CH3:27])([CH3:28])[CH3:29]

참가 물질

7

반응물 3

HCID 10340Sodium CarbonateHCID 2762707(2,6-Dimethoxypyridin-3-yl)boronic acidHCID 67286866N-{4-[(E)-2-(5-bromo-3-tert-butyl-2-methoxy-phenyl)-vinyl]-3-methoxymethyl-phenyl}-methanesulfonamide

생성물 1

HCID 68537390N-(4-{(E)-2-[3-tert-butyl-5-(2,6-dimethoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-3-methoxymethyl-phenyl) methanesulfonamide수율 79.2%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

step 1—A sealed tube containing 315 (117 mg, 0.243 mmol), 2,6-dimethoxy-pyridin-3-yl boronic acid (53 mg, 0.290 mmol, CASRN 221006-70-8), Pd(PPh3)4 (28 mg, 0.024 mmol), Na2CO3 (76 mg, 0.717 mmol) in a mixture of MeOH (3 mL) and DCM (1 mL) was irradiated in a microwave reactor at 115° C. for 30 minutes. The reaction mixture was concentrated, diluted with EtOAc, washed with brine and dried (Na2SO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (20% to 30% EtOAc) to afford 104 mg (79%) of N-(4-{(E)-2-[3-tert-butyl-5-(2,6-dimethoxy-pyridin-3-yl)-2-methoxy-phenyl]-vinyl}-3-methoxymethyl-phenyl) methanesulfonamide (322) as a colorless oil.

후처리

  1. customstep 1—A sealed tube
  2. customwas irradiated in a microwave reactor at 115° C. for 30 minutes
  3. concentrationThe reaction mixture was concentrated
  4. additiondiluted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (20% to 30% EtOAc)

출처 및 근거

ORD 기록
ord-3feb1da521004014be8e809ee5a57147
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273773B2

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