Hydrochloric Acid → Methyl 3-aminoisoquinoline-8-carboxylate

HRID 920254노트

반응식

HRID 920254 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

HCID 89524691Methyl 3-aminoisoquinoline-8-carboxylate수율 90%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-bcafa59648824708b402f5d27ff68b42
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273040B2

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