Sodium Carbonate → 10-(4-benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene

HRID 2251104Notes

Reaction equation

Cl[C:2]1[N:3]2[C:7]([N:8]=[C:9]3[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=13)=[CH:6][CH:5]=[N:4]2.[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[N:3]3[C:7]([N:8]=[C:9]4[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C:10]=24)=[CH:6][CH:5]=[N:4]3)=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 10-chloro-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (221 mg, 1.0 mmol) in toluene (4 mL) was added 4-benzyloxyphenyl boronic acid (100 mg, 2.0 mmol), tetrakis(triphenylphosphine) palladium (5.7 mg, 0.0047 mmol), and 2M aq Na2CO3 (1.0 mL, 2.0 mmol). The reaction was flushed with argon and stirred at 80° C. overnight. The solution was cooled, followed by dilution with EtOAc (3 mL). The organic layer was washed with H2O, brine, dried over MgSO4, and concentrated. The residue was purified via flash chromatography (5-30% EtOAc/Hexane) to provide 10-(4-benzyloxy-phenyl)-6,7,8,9-tetrahydro-5H-1,4,10a-triaza-cyclohepta[f]indene (200 mg, 54% yield).

Workup

customThe reaction was flushed with argon
temperatureThe solution was cooled
washThe organic layer was washed with H2O, brine
dry with materialdried over MgSO4
concentrationconcentrated
customThe residue was purified via flash chromatography (5-30% EtOAc/Hexane)

Sources & evidence

ORD record: ord-86619fc5ab9e4eed868595b26ae3aa7d
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319103B2

Reaction notes

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