4-Methoxybenzylamine → HCID 70255147, compound

HRID 850630Notes

Reaction equation

[C:1]([O:5][C:6](=[O:34])[CH2:7][C@H:8]([N:18]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28](Br)[N:27]=2)[C:19]1=[O:33])[C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)([CH3:4])([CH3:3])[CH3:2].CC([O-])(C)C.[Na+].[CH3:41][O:42][C:43]1[CH:50]=[CH:49][C:46]([CH2:47][NH2:48])=[CH:45][CH:44]=1>C1(C)C=CC=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].C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.[Fe+2]>[C:1]([O:5][C:6](=[O:34])[CH2:7][C@@H:8]([C:9]1[CH:10]=[N:11][CH:12]=[C:13]([O:15][CH2:16][CH3:17])[CH:14]=1)[N:18]1[CH2:22][CH2:21][N:20]([CH2:23][CH2:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:48][CH2:47][C:46]3[CH:49]=[CH:50][C:43]([O:42][CH3:41])=[CH:44][CH:45]=3)[N:27]=2)[C:19]1=[O:33])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 110 °C

Procedure

To a stirred solution of 20-11 (0.075 g, 0.142 mmol) in toluene (3 mL) was added Pd(DBA)2 (0.0041 g, 0.0071 mmol), DPPF (0.0039 g, 0.0071 mmol), and NaOt-Bu (0.0163 g, 0.170 mmol) followed by p-methoxybenzylamine (0.0204 mL, 0.156 mmol). The resulting solution was heated at 110° C. for 2 hours. The solution was cooled and the solvent was removed in vacuo. The product was purified by silica gel chromatography (10% EtOH/EtOAc) to give (20-12.

Workup

temperatureThe solution was cooled
customthe solvent was removed in vacuo
customThe product was purified by silica gel chromatography (10% EtOH/EtOAc)
customto give (20-12

Sources & evidence

ORD record: ord-095c85b651c74d648480e80eb02e88b9
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017926

Reaction notes

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