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Ethanol → 4-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]methyl-amino}-benzoic Acid Tert-butyl Ester

HRID 1755162
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HRID 1755162 반응식
[C:1]([O:5][C:6](=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:15]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[C:16](=[O:25])[NH:17][C:18]2[CH:23]=[CH:22][C:21](I)=[CH:20][CH:19]=2)[CH3:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C(O)C.C([O-])([O-])=O.[Na+].[Na+].[O:46]1[C:50](B(O)O)=[CH:49][C:48]2[CH:54]=[CH:55][CH:56]=[CH:57][C:47]1=2>COCCOC.O>[C:1]([O:5][C:6](=[O:36])[C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH:15]([C:16](=[O:25])[N:17]([C:47]2[O:46][C:50]3=[CH:49][CH:48]=[CH:54][C:55]3=[CH:56][CH:57]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:26]2[CH:31]=[CH:30][C:29]([C:32]([CH3:35])([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[CH3:14])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 674863434-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic Acid Tert-butyl Ester

생성물 1

HCID 674866384-{[(4-Benzofuran-2-yl-phenylcarbamoyl)-(4-tert-butyl-phenyl)-methyl]methyl-amino}-benzoic Acid Tert-butyl Ester수율 125.2%

시약·촉매·용매 2

HCID 962Water용매2회HCID 80711,2-Dimethoxyethane용매

실험 절차

4-{[(4-tert-Butyl-phenyl)-(4-iodo-phenylcarbamoyl)-methyl]-methyl-amino}-benzoic acid tert-butyl ester (120 mg, 0.19 mmol) was taken up in 8 mL of DME, 4 mL of ethanol and 2 mL of water. Na2CO3 (81 mg, 2.4 mmol), PdCl2(O-tolyl)2, (15 mg, 0.0019 mmol) and benzo[B]furan-2-boronic acid (62 mg, 0.38 mmol) were then added, flushed with nitrogen and heated to reflux for 1 h. Cooled to RT, EtOAc (20 mL) was added, and filtered through a plug of celite. The solvents were removed under reduced pressure to give a yellow viscous solid. Water was added to the solid to give a yellow precipitate, which was filtered and triturated with methanol to give 140 mg of a white solid. LCMS (M+1=589.6)

후처리

  1. customflushed with nitrogen
  2. temperatureheated
  3. temperatureto reflux for 1 h
  4. additionEtOAc (20 mL) was added
  5. filtrationfiltered through a plug of celite
  6. customThe solvents were removed under reduced pressure
  7. customto give a yellow viscous solid
  8. customto give a yellow precipitate, which
  9. filtrationwas filtered
  10. customtriturated with methanol

출처 및 근거

ORD 기록
ord-16f748cf67ee4f629b1d598deeff394d
출처 데이터셋
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09169201B2

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