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Sodium Carbonate → 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

HRID 595567
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HRID 595567 반응식
[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8](I)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1.[CH:22]([C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)=[O:23].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.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]>[Br:1][C:2]1[C:3]([N:16]([CH3:21])[S:17]([CH3:20])(=[O:19])=[O:18])=[CH:4][C:5]2[O:9][C:8]([C:27]3[CH:28]=[CH:29][C:24]([CH:22]=[O:23])=[CH:25][CH:26]=3)=[C:7]([C:11]([NH:13][CH3:14])=[O:12])[C:6]=2[CH:15]=1
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 5910734-Formylphenylboronic AcidHCID 903324695-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

생성물 1

HCID 903324885-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide수율 58.1%

시약·촉매·용매 2

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
촉매
HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

To a degassed solution of compound 5-bromo-2-iodo-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (400 mg, 0.82 mmol), (4-formylphenyl)boronic acid (110 mg, 0.74 mmol) and Na2CO3 (174 mg, 1.6 mmol) in DMF (4 mL) was added Pd(dppf)Cl2 (20 mg) under N2, and the mixture was stirred at 100° C. for 2 h. After the solvent was removed, the residue was purified by column chromatography (DCM:EtOAc=10:1) to give the product of compound 5-bromo-2-(4-formylphenyl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide (200 mg, yield: 52%). 1H-NMR (CDCl3, 400 MHz) 10.09 (s, 1H), 8.09˜8.15 (m, 3H), 8.02 (s, 2H), 7.75 (s, 1H), 5.90 (s, 1H), 3.36 (s, 3H), 3.11 (s, 3H), 3.05 (d, J=4.8 Hz, 3H). MS (M+H)+: 465/467.

후처리

  1. customAfter the solvent was removed
  2. customthe residue was purified by column chromatography (DCM:EtOAc=10:1)

출처 및 근거

ORD 기록
ord-ddd8807406074a83991b30b4a5aef0ec
출처 데이터셋
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09242998B2

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