Sodium Carbonate → 2-(5-Acetyl-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocin-9-yl)-benzamide

HRID 2220208Notes

Reaction equation

[Cl:1][C:2]1[CH:29]=[CH:28][C:5]2[N:6]([C:25](=[O:27])[CH3:26])[CH2:7][C:8]3[CH:15]=[CH:14][C:13](B4OC(C)(C)C(C)(C)O4)=[CH:12][C:9]=3[CH2:10][CH2:11][C:4]=2[CH:3]=1.Br[C:31]1[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=1[C:33]([NH2:35])=[O:34].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>[C:25]([N:6]1[CH2:7][C:8]2[CH:15]=[CH:14][C:13]([C:31]3[CH:39]=[CH:38][CH:37]=[CH:36][C:32]=3[C:33]([NH2:35])=[O:34])=[CH:12][C:9]=2[CH2:10][CH2:11][C:4]2[CH:3]=[C:2]([Cl:1])[CH:29]=[CH:28][C:5]1=2)(=[O:27])[CH3:26]

Participants

Conditions

Temperature: 80 °C

Procedure

A 2 mL conical vial was charged with Example 22B (10 mg, 0.024 mmol), 2-bromo-benzamide (7 mg, 0.036 mmol) and Pd(PPh3)4 (3 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 2-(5-Acetyl-2-chloro-5,6,11,12-tetrahydro-dibenzo[b,f]azocin-9-yl)-benzamide (5.6 mg, 58%). HPLC Rt=1.62(b) min. m/z=405 (M+H+).

Workup

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-4ae594f30b904ad8bb679343b36bea78
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07417040B2

Reaction notes

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