Tetrahydrofuran → HCID 178459033、化合物

HRID 549489

反応式

HRID 549489 の反応式
B1C2CCCC1CCC2.C1COCC1.[CH3:15][C:16]([OH:20])([CH:18]=[CH2:19])[CH3:17].C([O-])([O-])=O.[Cs+].[Cs+].[As](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.Br[C:47]1[CH:48]=[C:49]2[C:71](=[CH:72][CH:73]=1)[C:57]1[NH:58][C:59]([C:61]3[C:68]([C:69]#[N:70])=[CH:67][CH:66]=[CH:65][C:62]=3[C:63]#[N:64])=[N:60][C:56]=1[C:55]1[CH:54]=[CH:53][C:52]([Cl:74])=[CH:51][C:50]2=1>[Cl-].[Na+].O.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].O.CN(C=O)C>[Cl:74][C:52]1[CH:51]=[C:50]2[C:55](=[CH:54][CH:53]=1)[C:56]1[NH:60][C:59]([C:61]3[C:68]([C:69]#[N:70])=[CH:67][CH:66]=[CH:65][C:62]=3[C:63]#[N:64])=[N:58][C:57]=1[C:71]1[CH:72]=[CH:73][C:47]([CH2:19][CH2:18][C:16]([OH:20])([CH3:17])[CH3:15])=[CH:48][C:49]2=1

参加物

11

反応物 6

HCID 8028TetrahydrofuranHCID 82572-Methyl-3-buten-2-olHCID 10796Cesium carbonateHCID 11773TriphenylarsineHCID 789669-Borabicyclo(3.3.1)nonaneHCID 178509773HCID 178509773、化合物

生成物 1

HCID 178459033HCID 178459033、化合物

試薬・触媒・溶媒 4

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

To a solution of 9-BBN in THF (24 ml, 12 mmol, 0.5 M) was added 2-methyl-3-buten-2-ol (345 mg, 4.0 mmol) and the resulting solution was stirred under N2 at rt for overnight. In a second flask charged with PdCl2(dppf) (324 mg, 0.40 mmol), Cs2CO3 (2.4 g, 8.0 mmol) and Ph3As (124 mg, 0.4 mmol) was added 2-(6-bromo-9-chloro-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile from Example 36, DMF (24 ml) and H2O (0.88 ml) and the mixture was stirred under N2 for 5 minutes. The hydroboration mixture was then transferred to the second flask and the resulting reaction suspension was stirred at rt under N2 for 5 days. After being treated with brine, the aqueous phase was extracted with EtOAc and the combined organic solution was washed with water and brine, dried over MgSO4. After removing the drying agent by filtration, the solution was concentrated under reduced pressure and the residue was purified by silica gel chromatography (50% EtOAc/Hexane) to yield 600 mg of 2-[9-chloro-6-(3-hydroxy-3-methylbutyl)-1H-phenanthro[9,10-d]imidazol-2-yl)isophthalonitrile as a yellow solid. 1H NMR (400 MHz, Acetone): δ 13.10 (s br, 1H); 8.94 (s, 1H); 8.77 (s, 1H); 8.70-8.60 (m br, 2H); 8.39 (d, 2H); 8.03 (t, 1H); 7.75 (dd, 1H); 7.69 (dd, 1H); 4.92 (s, 1H); 3.05 (m, 2H); 1.95 (m, 2H); 1.33 (s, 6H).

後処理

  1. stirringthe mixture was stirred under N2 for 5 minutes
  2. customthe resulting reaction suspension
  3. stirringwas stirred at rt under N2 for 5 days
  4. extractionthe aqueous phase was extracted with EtOAc
  5. washthe combined organic solution was washed with water and brine
  6. dry with materialdried over MgSO4
  7. customAfter removing the drying agent
  8. filtrationby filtration
  9. concentrationthe solution was concentrated under reduced pressure
  10. customthe residue was purified by silica gel chromatography (50% EtOAc/Hexane)

出典と根拠

ORDレコード
ord-766fdcca591c4c6596bf237194162126
出典データセット
uspto-grants-2011_05
特許番号
US07943649B2

関連ノート

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