Nitrogen → 1,1-dimethylethyl 6-[3-(aminocarbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

HRID 70315

反応式

HRID 70315 の反応式
[NH2:1][C:2]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)=[O:3].FC(F)(F)S(O[C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][CH:28]=1)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][CH2:22]2)(=O)=O.N#N.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.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.O>[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH2:25][N:24]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:23][CH2:22]3)[CH:7]=[CH:8][CH:9]=1)=[O:3]

参加物

8

反応物 4

HCID 947NitrogenHCID 62657Potassium Phosphate, TribasicHCID 2737814(3-Carbamoylphenyl)boronic acidHCID 10091216Tert-butyl 6-(trifluoromethylsulfonyloxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate

生成物 1

HCID 582763421,1-dimethylethyl 6-[3-(aminocarbonyl)phenyl]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A solution of 3-(aminocarbonyl)phenyl boronic acid (0.663 g; 4.0 mmol), 1,1-dimethylethyl 6-{[(trifluoromethyl)sulfonyl]oxy}-3,4-dihydro-2(1H)-isoquinoline carboxylate (1.28 g; 3.35 mmol; Ex V-16) in DMF (10 mL) was sparged with N2 for 10 min, K3PO4 (1.7 g; 8.0 mmol) and Pd(PPh3)4 (0.193 g; 0.17 mmol) were added and the mixture was stirred at 100° C. for 2 h. Upon cooling, the mixture was poured into water and extracted with EtOAc (×3). Combined organics were washed (H2O, brine), and dried over Na2SO4. Residual solids were collected from the aqueous layer by filtration, air-dried, dissolved in hot EtOH and combined with the dried EtOAc extracts. The whole was adsorbed onto a minimal amount of silica gel and purified by flash chromatography (EtOAc/hexanes), affording the title compound as a as a colorless solid. LC/MS (method B) 2.69 min; m/z 297 ([M−C4H8]+H, 70%), 253 ([M−Boc]+H, 74%).

後処理

  1. temperatureUpon cooling
  2. extractionextracted with EtOAc (×3)
  3. washCombined organics were washed (H2O, brine)
  4. dry with materialdried over Na2SO4
  5. filtrationResidual solids were collected from the aqueous layer by filtration
  6. customair-dried
  7. dissolutiondissolved in hot EtOH
  8. custompurified by flash chromatography (EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1348729079e345cb9e93a57d7063f141
出典データセット
uspto-grants-2014_09
特許番号
US08822518B2

関連ノート

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