Benzophenone imine → (2-Amino-pyridin-4-yl)-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-methanone

HRID 2390802노트

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HRID 2390802 반응식
[C:1]([C:5]1[C:6]([O:28][CH3:29])=[C:7]([C:19]([C:21]2[CH:26]=[CH:25][N:24]=[C:23](Cl)[CH:22]=2)=[O:20])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C(=[NH:43])(C1C=CC=CC=1)C1C=CC=CC=1.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:43][C:23]1[CH:22]=[C:21]([C:19]([C:7]2[CH:8]=[C:9]([C:11]3[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=3)[CH:10]=[C:5]([C:1]([CH3:3])([CH3:2])[CH3:4])[C:6]=2[O:28][CH3:29])=[O:20])[CH:26]=[CH:25][N:24]=1

참가 물질

6

반응물 4

HCID 136809Benzophenone imineHCID 634876Binap, (A+-)-HCID 23676156Sodium t-butoxideHCID 86638337[3-Tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-(2-chloro-pyridin-4-yl)-methanone

생성물 1

HCID 67069931(2-Amino-pyridin-4-yl)-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-methanone

시약·촉매·용매 1

HCID 9811564Bis(dibenzylideneacetone)palladium촉매

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온도
80 °C

실험 절차

step 3—A flask containing 42 (106 mg, 0.259 mmol), benzophenone imine (0.070 mL, 0.417 mmol), Pd2(dba)3 (11.5 mg, 0.013 mmol), racemic BINAP (23.8 mg, 0.038 mmol), and sodium tert-butoxide (35 mg, 0.364 mmol) was purged with argon 3 times before toluene (5 mL) was added. The reaction was heated overnight at 80° C. then cooled to RT. The reaction mixture was diluted with EtOAc, filtered through CELITE, and the filtrate was concentrated. The residue was taken up in a mixture of MeOH (5 mL) and hydroxylamine (50% wt solution in water, 0.5 mL) and stirred overnight at RT before it was concentrated. The crude residue was purified by SiO2 chromatography eluting with an EtOAc/hexane gradient (25 to 75% EtOAc) to afford (2-amino-pyridin-4-yl)-[3-tert-butyl-2-methoxy-5-(2-methoxy-pyridin-3-yl)-phenyl]-methanone (44) as a pale yellow oil.

후처리

  1. customwas purged with argon 3 times before toluene (5 mL)
  2. additionwas added
  3. temperaturethen cooled to RT
  4. additionThe reaction mixture was diluted with EtOAc
  5. filtrationfiltered through CELITE
  6. concentrationthe filtrate was concentrated
  7. additionThe residue was taken up in a mixture of MeOH (5 mL) and hydroxylamine (50% wt solution in water, 0.5 mL)
  8. concentrationwas concentrated
  9. customThe crude residue was purified by SiO2 chromatography
  10. washeluting with an EtOAc/hexane gradient (25 to 75% EtOAc)

출처 및 근거

ORD 기록
ord-b4c9845cf3a0435faea072184ea876ce
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273773B2

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