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Potassium Carbonate → 3-(4''-Amino-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-7'-yl)-5-fluorobenzonitrile

HRID 1468235
ノート
印刷プレビュー

反応式

HRID 1468235 の反応式
[C:1]([C:3]1[CH:4]=[C:5](B(O)O)[CH:6]=[C:7]([F:9])[CH:8]=1)#[N:2].Br[C:14]1[CH:31]=[C:30]2[C:17]([CH2:18][CH2:19][C:20]3([C:23]42[N:27]=[C:26]([NH2:28])[C:25]([CH3:29])=[N:24]4)[CH2:22][CH2:21]3)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].CC([PH+](C(C)(C)C)CCCS([O-])(=O)=O)(C)C>[Cl-].[Na+].O.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl.CCOC(C)=O.O>[NH2:28][C:26]1[C:25]([CH3:29])=[N:24][C:23]2([C:30]3[C:17](=[CH:16][CH:15]=[C:14]([C:5]4[CH:4]=[C:3]([CH:8]=[C:7]([F:9])[CH:6]=4)[C:1]#[N:2])[CH:31]=3)[CH2:18][CH2:19][C:20]32[CH2:21][CH2:22]3)[N:27]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

9

反応物 4

HCID 11430Potassium CarbonateHCID 23435605(3-Cyano-5-fluorophenyl)boronic acidHCID 249491873-(Di-tert-butylphosphonium)propane sulfonateHCID 727146587'-Bromo-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

生成物 1

HCID 727146593-(4''-Amino-5''-methyl-3',4'-dihydrodispiro[cyclopropane-1,2'-naphthalene-1',2''-imidazol]-7'-yl)-5-fluorobenzonitrile
収率 86.4%

試薬・触媒・溶媒 4

HCID 178479786HCID 178479786、化合物触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

反応条件

温度
100 °C

実験手順

3-Cyano-5-fluorophenylboronic acid (83 mg, 0.50 mmol) was added to 7′-bromo-5″-methyl-3′,4′-dihydrodispiro[cyclopropane-1,2′-naphthalene-1′,2″-imidazol]-4″-amine (Example 1, 100 mg, 0.31 mmol) in dry 2-Me THF (2.85 mL), followed by aq. potassium carbonate (2.0 M, 0.471 mL, 0.94 mmol). Argon was bubbled through the mixture for one min. and then sodium tetrachloropalladate(II) (9.3 mg, 0.03 mmol) and 3-(di-tert-butylphosphonium)propane sulfonate (16.9 mg, 0.06 mmol) were added and the mixture was heated in a microwave reactor for 60 min at 100° C. Water, brine, 2-Me THF and EtOAc were added to the mixture and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with brine and water. The organic phase was dried (Na2SO4), filtered and concentrated. Recrystallization from MeOH and CHCl3 and purification by preparative HPLC gave the title compound (96 mg, 85% yield).

後処理

  1. customArgon was bubbled through the mixture for one min.
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic phases were washed with brine and water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customRecrystallization
  9. customfrom MeOH and CHCl3 and purification by preparative HPLC

出典と根拠

ORDレコード
ord-324eb7a67a21415dbeed41a9f9928ae1
出典データセット
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09000184B2

反応ノート

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