Sodium Carbonate → HCID 72557551, compound

HRID 2220209Notes

Reaction equation

CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]3[CH2:19][N:18]([C:20](=[O:22])[CH3:21])[C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=4[CH:15]=[CH:14][C:13]=3[CH:27]=2)O1.[Br:29][C:30]1[CH:35]=[CH:34][CH:33]=[C:32](Br)[N:31]=1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:29][C:30]1[N:31]=[C:32]([C:9]2[CH:10]=[CH:11][C:12]3[CH2:19][N:18]([C:20](=[O:22])[CH3:21])[C:17]4[CH:23]=[CH:24][CH:25]=[CH:26][C:16]=4[CH:15]=[CH:14][C:13]=3[CH:27]=2)[CH:33]=[CH:34][CH:35]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A 2 mL conical vial was charged with 1-[9-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)-6H-dibenzo[b,f]azocin-5-yl]-ethanone (prepared by the method described in Example 2A starting with 2)(30 mg, 0.08 mmol), 2,6-Dibromo-pyridine (39 mg, 0.18 mmol) and Pd(PPh3)4 (9 mg). The vial was evacuated and purged with argon. EtOH (0.5 mL) and toluene (0.5 mL) were added, followed by 2M aqueous Na2CO3 (0.036 mL, 0.072 mmol). The reaction was heated to 80° C. until disappearance of the starting material was noted. The reaction was cooled to room temperature and concentrated. The product was purified by reversed-phase HPLC to afford Example 206A (18.5 mg, 60%).

Workup

customprepared by the method
customThe vial was evacuated
custompurged with argon
additionEtOH (0.5 mL) and toluene (0.5 mL) were added
temperatureThe reaction was cooled to room temperature
concentrationconcentrated
customThe product was purified by reversed-phase HPLC

Sources & evidence

ORD record: ord-2849a0a2d15c45e0975b364fbd09b293
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417040B2

Reaction notes

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