Dichloromethane → 4-[3-(2-Methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-benzamide

HRID 2388950노트

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HRID 2388950 반응식
Br[C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[O:17][CH3:18])=[N:9][NH:8][C:5]2=[N:6][CH:7]=1.[CH3:19][NH:20][C:21]([C:23]1[CH:28]=[CH:27][C:26](B(O)O)=[CH:25][CH:24]=1)=[O:22].ClCCl>C(#N)C.C([O-])(O)=O.[Na+].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:18][O:17][C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:26]3[CH:27]=[CH:28][C:23]([C:21]([NH:20][CH3:19])=[O:22])=[CH:24][CH:25]=3)[CH:3]=2)[NH:8][N:9]=1

참가 물질

7

반응물 3

HCID 6344DichloromethaneHCID 27735264-(Methylcarbamoyl)benzeneboronic acidHCID 178489372HCID 178489372, 화합물

생성물 1

HCID 1784852994-[3-(2-Methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-benzamide수율 20%

시약·촉매·용매 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 6342Acetonitrile용매HCID 516892Sodium Bicarbonate용매

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온도
130 °C

실험 절차

To a solution of 5-bromo-3-(2-methoxy-phenyl)-1H-pyrazolo[3,4-b]pyridine (26 mg, 0.085 mmol) in acetonitrile (1 mL) and saturated aqueous NaHCO3 (1 mL) in a microwave vial was added 4-(N-methylaminocarbonyl)phenylboronic acid (17 mg, 0.094 mmol) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (II), complex with dichloromethane (1:1) (3.5 mg, 0.004 mmol). The vial was capped, flushed with N2, evacuated under vacuum, and heated in a microwave at 130° C. for 1800 seconds. The material was extracted into EtOAc and the organic layer was dried over Na2SO4. The material was adsorbed onto SiO2 and purified by flash chromatography in a EtOAc (containing 10% MeOH) and hexane gradient. The clean fractions were concentrated via rotary evaporation to afford the title compound as a white powder (5.9 mg, 20% yield). 1H NMR (500 MHz, CD3OD) δ 8.85 (s, 1H), 8.41 (s, 1H), 7.94 (d, J=8.5 Hz, 2H), 7.78 (d, J=8.5 Hz, 2H), 7.67 (d, J=7.5 Hz, 1H), 7.48 (t, 7.0 Hz, 1H), 7.21 (d, J=8.5 Hz, 1H), 7.11 (t, J=7.0 Hz, 1H), 3.89 (s, 3H), 2.95 (s, 3H). MS: m/z 359.1 [M+H+].

후처리

  1. customThe vial was capped
  2. customflushed with N2
  3. customevacuated under vacuum
  4. extractionThe material was extracted into EtOAc
  5. dry with materialthe organic layer was dried over Na2SO4
  6. custompurified by flash chromatography in a EtOAc (containing 10% MeOH) and hexane gradient
  7. concentrationThe clean fractions were concentrated via rotary evaporation

출처 및 근거

ORD 기록
ord-886eab00f2734f0cbb3948fa708740f5
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08268994B2

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