Hydrochloric Acid → Methyl 3-aminoisoquinoline-8-carboxylate

HRID 920254ノート

反応式

HRID 920254 の反応式
Cl[C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([O:14][CH3:15])=[O:13].C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[Li+].C[Si]([N-:46][Si](C)(C)C)(C)C.Cl>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1COCC1>[NH2:46][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][C:6]=2[C:12]([O:14][CH3:15])=[O:13]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 2733832Lithium HexamethyldisilazideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 89524931Methyl 3-chloroisoquinoline-8-carboxylate

生成物 1

HCID 89524691Methyl 3-aminoisoquinoline-8-carboxylate収率 90%

試薬・触媒・溶媒 2

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

A 20 mL microwave vial was charged with methyl 3-chloroisoquinoline-8-carboxylate (0.56 g, 2.57 mmol), [1,1′-biphenyl]-2-yldicyclohexylphosphine (90 mg, 0.257 mmol), LHMDS (3.0 mL, 3.08 mmol) and Pd2(dba)3 (118 mg, 0.125 mmol) and then with 12 mL of THF. Reaction mixture was capped and stirred at 65° C. overnight. Then 2M HCl (1.2 mL, 2.57 mmol) was added and stirred at rt for 20 min. The reaction mixture was filtered and added with sat bi carb. Extracted with EtOAc. Combined organic layer was dried, filtered, concentrated in vacuo. Purified by silica gel chromatography (0-50% EtOAc in hexane) yielded 90% Methyl 3-aminoisoquinoline-8-carboxylate (27-2).

後処理

  1. customReaction mixture
  2. customwas capped
  3. stirringstirred at rt for 20 min
  4. filtrationThe reaction mixture was filtered
  5. additionadded
  6. extractionExtracted with EtOAc
  7. customCombined organic layer was dried
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customPurified by silica gel chromatography (0-50% EtOAc in hexane)

出典と根拠

ORDレコード
ord-bcafa59648824708b402f5d27ff68b42
出典データセット
uspto-grants-2016_03
特許番号
US09273040B2

反応ノート

読み込み中…