Ethyl Acetate → 7-(5-methylthiophen-2-yl)-4-(pyrimidin-2-ylmethyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one

HRID 717049Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[CH2:7][N:8]1[C:14](=[O:15])[C:13]2[CH:16]=[C:17](B3OC(C)(C)C(C)(C)O3)[CH:18]=[CH:19][C:12]=2[O:11][CH2:10][CH2:9]1.Br[C:30]1[S:31][C:32]([CH3:35])=[CH:33][CH:34]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C.O.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[CH3:35][C:32]1[S:31][C:30]([C:17]2[CH:18]=[CH:19][C:12]3[O:11][CH2:10][CH2:9][N:8]([CH2:7][C:2]4[N:1]=[CH:6][CH:5]=[CH:4][N:3]=4)[C:14](=[O:15])[C:13]=3[CH:16]=2)=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 4-(pyrimidin-2-ylmethyl)-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one (50 mg, 0.13 mmol), 2-bromo-5-methylthiophene (28 mg, 0.156 mmol), cesium carbonate (128 mg, 0.39 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium (9 mg, 0.013 mmol) was dissolved in a degassed mixture of DMF and water 3/1.5 (4.5 ml). The mixture was heated in microwave at 85° C. for 40 min. The mixture was poured into EtOAc and washed with water and brine. The organic layer was collected, dried over sodium sulfate and loaded onto silica gel. A flash column (5% MeOH in EtOAc) and reverse phase chromatography gave 7-(5-methylthiophen-2-yl)-4-(pyrimidin-2-ylmethyl)-3,4-dihydrobenzo[f][1,4]oxazepin-5(2H)-one.

Workup

washwashed with water and brine
customThe organic layer was collected
dry with materialdried over sodium sulfate

Sources & evidence

ORD record: ord-81a502d5d5b7402e92a34c8ce65ac016
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193694B2

Reaction notes

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