Potassium Hydroxide → HCID 58167949, compound
Reaction equation
Cl[C:2]1[CH:16]=[CH:15][C:5]2[C:6](=[O:14])[NH:7][C:8]3[C:13]([C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][N:9]=3.[NH2:17][CH2:18][C:19]1[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[OH-].[K+]>C(O)(C)(C)C.CN(C=O)C.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]>[O:14]=[C:6]1[C:5]2[CH:15]=[CH:16][C:2]([NH:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=3)=[CH:3][C:4]=2[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7]1Participants
8
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 125 °C
Procedure
6 (100 mg, 0.43 mmol), 4-(aminomethyl)benzoic acid (0.19 mL, 1.30 mmol), Pd2(dba)3 (16 mg, 0.02 mmol), X-Phos (24 mg, 0.05 mmol), and KOH (73 mg, 1.30 mmol) were suspended in tert-butanol (3 mL), and stirred for 10 minutes at 125° C. via microwave. The reaction mixture was diluted with DMF and filtered. The crude product was purified directly via prep-LC-MS to provide 453 (11 mg, 7% yield) as a white powder. LC-MS (M+H=346, obsd.=346). 1H NMR (400 MHz, DMSO-D6) δ 11.49 (s, 0H), 8.55 (s, 2H), 8.41 (s, 1H), 7.95 (d, J=29.0, 3H), 7.56 (s, 2H), 7.38 (s, 2H), 7.25 (s, 1H), 6.97 (s, 1H), 4.60 (s, 2H).
Workup
- filtrationfiltered
- customThe crude product was purified directly via prep-LC-MS
Sources & evidence
- ORD record
- ord-da9fc88d0d8545cc8927858c426159a4
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08735584B2
Reaction notes
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