3-Nitrophenylboronic Acid → HCID 71075495, compound

HRID 1028109Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6](B(O)O)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].Br[C:14]1[S:18][C:17]([N:19]2[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]2)=[N:16][CH:15]=1.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N+:1]([C:4]1[CH:5]=[C:6]([C:14]2[S:18][C:17]([N:19]3[CH2:24][CH2:23][CH:22]([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:21][CH2:20]3)=[N:16][CH:15]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

Conditions

Temperature: 100 °C

Procedure

A mixture of (3-nitrophenyl)boronic acid (188 mg, 1.13 mmol), ethyl 1-(5-bromo-1,3-thiazol-2-yl)piperidine-4-carboxylate (300 mg, 0.94 mmol), palladium(II) acetate (10.5 mg, 0.047 mmol), and tris(2-methylphenyl)phosphane (286 mg, 0.94 mmol) in 1,2-dimethoxyethane (1.9 mL) and 2M aqueous sodium carbonate (0.7 mL, 1.4 mmol) was heated to 100° C. in the microwave for 30 minutes. After cooling to room temperature, the mixture was diluted with ethyl acetate (100 mL) and washed with 1:1 water:brine (50 mL). The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by CombiFlash (0-40% ethyl acetate/hexanes) provided 79 mg (0.22 mmol, 23% yield) of ethyl 1-[5-(3-nitrophenyl)-1,3-thiazol-2-yl]piperidine-4-carboxylate as a yellow solid.

Workup

temperatureAfter cooling to room temperature
washwashed with 1:1 water
dry with materialThe organic layer was dried over sodium sulfate
concentrationconcentrated in vacuo
customPurification by CombiFlash (0-40% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-f5f96897abd84b53a24952aac40b5af9
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08735417B2

Reaction notes

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