Sodium Hydroxide → 3-Amino-7-vinylquinoline-2-carboxylic acid
Reaction equation
C(OC([NH:11][C:12]1[C:13]([C:23]([O:25]CC)=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17](Br)[CH:16]=2)=O)C1C=CC=CC=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:36][C:37]1(C)C(C)(C)OB(C=C)O1.[OH-].[Na+]>C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.NC1C=CC=CC=1C1C=CC=CC=1[Pd]Cl.O.O1CCOCC1>[NH2:11][C:12]1[C:13]([C:23]([OH:25])=[O:24])=[N:14][C:15]2[C:20]([CH:21]=1)=[CH:19][CH:18]=[C:17]([CH:36]=[CH2:37])[CH:16]=2Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 80 °C
Procedure
Ethyl 3-{[(benzyloxy)carbonyl]amino}-7-bromoquinoline-2-carboxylate (1.50 g, 3.49 mmol), K3PO4 (1.48 g, 6.97 mmol), 1,4-dioxane (45 mL), water (7.5 mL) and 4,4,5,5-tetramethyl-2-vinyl-1,3,2-dioxaborolane (0.80 g, 5.2 mmol) were added to a flask. The reaction mixture was purged with nitrogen for 10 min., then dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (0.18 g, 0.23 mmol) was added. The flask was then sealed and the reaction mixture was heated at 80° C. for 1 h, then allowed to cool to room temperature. After the reaction mixture was allowed to cool, aq. NaOH (2.5 M; 45 mL) was added, the resulting cloudy mixture was then heated at 95° C. for 3 h, and then allowed to cool. The crude product formed as a precipitate, which was collected by vacuum filtration and used in the next step without further purification. LCMS calc. for C12H11N2O2 (M+H)+: m/z=215.2. Found: 215.0.
Workup
- customThe reaction mixture was purged with nitrogen for 10 min.
- customThe flask was then sealed
- temperatureto cool to room temperature
- temperatureto cool
- temperaturethe resulting cloudy mixture was then heated at 95° C. for 3 h
- temperatureto cool
Sources & evidence
- ORD record
- ord-319ef15571604013af1824a22eb5121c
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09278950B2
Reaction notes
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