Citric Acid → 3-(3-Aminoisoquinolin-7-yl)-4-methylbenzoic acid

HRID 468913ノート

反応式

HRID 468913 の反応式
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[C:7]([NH2:12])[N:8]=[CH:9]2)=[CH:4][CH:3]=1.[CH3:13][C:14]1[CH:22]=[CH:21][C:17]([C:18]([OH:20])=[O:19])=[CH:16][C:15]=1B1OC(C)(C)C(C)O1.C(=O)([O-])[O-].[K+].[K+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl.O.O1CCOCC1>[NH2:12][C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[C:2]([C:15]1[CH:16]=[C:17]([CH:21]=[CH:22][C:14]=1[CH3:13])[C:18]([OH:20])=[O:19])[CH:11]=2

参加物

8

反応物 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 529877577-Bromoisoquinolin-3-amineHCID 679763944-Methyl-3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)benzoic acid

生成物 1

HCID 679748773-(3-Aminoisoquinolin-7-yl)-4-methylbenzoic acid収率 68%

試薬・触媒・溶媒 3

HCID 11714597Bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II)触媒HCID 962Water溶媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of 7-bromoisoquinolin-3-amine (299.9 mg; 1.344 mmol), 4-methyl-3-(4,4,5-trimethyl-1,3,2-dioxaborolan-2-yl)benzoic acid (387.1 mg; 1.560 mmol), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (51.5 mg; 0.0727 mmol), potassium carbonate (569.3 mg; 4.119 mmol), dioxane (10 mL) and water (1 mL) was stirred at 90° C. for 24 hours and then cooled to room temperature. The reaction mixture was acidified with 10% aqueous citric acid (10 mL). The product was recovered as a red-brown precipitate via filtration, rinsed with water and ethyl acetate, and dried under vacuum to yield 253.4 mg (68%) of the title compound which was carried forward without additional purification. LCMS (ESI): M+H=279.2; 1H NMR (400 MHz, DMSO) δ 8.87 (s, 1H), 7.84 (d, J=7.9 Hz, 1H), 7.81 (d, J=13.1 Hz, 2H), 7.59 (d, J=8.6 Hz, 1H), 7.46 (t, J=9.5 Hz, 2H), 6.67 (s, 1H), 5.96 (s, 2H), 2.34 (s, 3H).

後処理

  1. temperaturecooled to room temperature
  2. filtrationThe product was recovered as a red-brown precipitate via filtration
  3. washrinsed with water and ethyl acetate
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-9490429e540947fb8839ee35dc86aaf6
出典データセット
uspto-grants-2014_01
特許番号
US08623889B2

反応ノート

読み込み中…