Hydrochloric Acid → HCID 89524792, compound
Reaction equation
Cl[C:2]1[N:3]=[CH:4][C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[C:10]=2[CH:11]=1.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[CH:6]=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[C:10]=2[CH:11]=1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 65 °C
Procedure
A 20 mL microwave vial was charged with methyl 3-chloroisoquinoline-5-carboxylate (0.36 g, 1.63 mmol), [1,1′-biphenyl]-2-yldicyclohexylphosphine (57 mg, 0.163 mmol), LHMDS (1.96 mL, 1.96 mmol) and Pd2(dba)3 (75 mg, 0.082 mmol) and then with 8 mL of THF. Reaction mixture was capped and stirred at 65° C. overnight. Then 2M HCl (4.08 mL, 8.17 mmol) was added and stirred at rt for 20 min. The reaction mixture was filtered and added with sat NaHCO3. Extracted with EtOAc. Combined organic layer was dried, filtered, concentrated in vacuo. Purified by silica gel chromatography (0-50% EtOAc in hexane) yielded 58% Methyl 3-aminoisoquinoline-5-carboxylate (26-2).
Workup
- customReaction mixture
- customwas capped
- stirringstirred at rt for 20 min
- filtrationThe reaction mixture was filtered
- additionadded with sat NaHCO3
- extractionExtracted with EtOAc
- customCombined organic layer was dried
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurified by silica gel chromatography (0-50% EtOAc in hexane)
Sources & evidence
- ORD record
- ord-24723fc4bb234dd2a55f02018042559d
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273040B2
Reaction notes
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