Cesium fluoride → 4-(1,2-Dimethyl-1H-imidazol-5-yl)-2-methoxyaniline

HRID 2205906Notes

Reaction equation

Br[C:2]1[N:6]([CH3:7])[C:5]([CH3:8])=[N:4][CH:3]=1.[CH3:9][O:10][C:11]1[CH:17]=[C:16](B2OC(C)(C)C(C)(C)O2)[CH:15]=[CH:14][C:12]=1[NH2:13].[F-].[Cs+]>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.COCCOC.CO>[CH3:7][N:6]1[C:2]([C:16]2[CH:15]=[CH:14][C:12]([NH2:13])=[C:11]([O:10][CH3:9])[CH:17]=2)=[CH:3][N:4]=[C:5]1[CH3:8]

Participants

Conditions

Temperature: 150 °C

Procedure

To a microwave vial was added 5-bromo-1,2-dimethyl-1H-imidazole (230 mg, 1.31 mmol), 2-methoxy-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (393 mg, 1.58 mmol), Pd(PPh3)4 (152 mg, 0.13 mmol), CsF (599 mg, 3.94 mmol) and DME/MeOH 3/1 (4 mL). The mixture was heated in a microwave at 150° C. for 1 hour. The reaction mixture was then filtered and concentrated onto silica gel and purified by Biotage silica gel column chromatography eluting with (EtOAc/MeOH 100/0 to 96/4) to give the title product as a light brown oil (120 mg, 42%). 1H NMR (500 MHz, CDCl3): δ 2.43 (s, 3H), 3.48 (s, 3H), 3.87 (s, 3H), 6.73-6.78 (m, 3H), 6.87 (s, 1H). LC (Method A)-MS (ESI, m/z) tR 0.49 min, 218 [(M+H+), 100%].

Workup

filtrationThe reaction mixture was then filtered
concentrationconcentrated onto silica gel
custompurified by Biotage silica gel column chromatography
washeluting with (EtOAc/MeOH 100/0 to 96/4)

Sources & evidence

ORD record: ord-91a655be8cb948b8b645bd70ad0a2a7c
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371319B2

Reaction notes

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