Cesium carbonate → 4-(3-Piperidin-1-yl-propyl)-1-(3-trifluoromethyl-phenyl)-[1,4]diazepan-5-one

HRID 1096233Notes

Reaction equation

[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:16](=[O:17])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.I[C:19]1[CH:20]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:22]=[CH:23][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[N:1]1([CH2:7][CH2:8][CH2:9][N:10]2[C:16](=[O:17])[CH2:15][CH2:14][N:13]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=3)[CH2:12][CH2:11]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of 0.02 g (0.10 mmol) of 4-(3-piperidin-1-yl-propyl)-[1,4]diazepan-5-one, 3-iodobenzotrifluoride 0.03 g (0.12 mmol), Pd(OAc)2 0.01 g (0.05 mmol), racemic-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl 0.03 g (0.05 mmol), cesium carbonate 0.16 g (0.5 mmol) in toluene (1 ml) was heated at 110° C. for 24 h. The reaction was then filtered, concentrated and the residue purified by preparative HPLC affording the title compound 0.1 g (26%) as a gum. MS: 384.2 (MH+).

Workup

filtrationThe reaction was then filtered
concentrationconcentrated
customthe residue purified by preparative HPLC

Sources & evidence

ORD record: ord-737db5099ac24804a816ad315ea6be4b
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08138175B2

Reaction notes

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