Bromobenzene → HCID 71523658, compound

HRID 1430588Notes

Reaction equation

[C:1]([CH:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([C:11]1[CH:16]=[C:15]([CH3:17])[CH:14]=[CH:13][C:12]=1[N:18]1[N:22]=[CH:21][CH:20]=[N:19]1)=[O:10])#[CH:2].Br[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(N(CC)CC)C>CN(C=O)C.[Cu]I.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>[CH3:17][C:15]1[CH:14]=[CH:13][C:12]([N:18]2[N:22]=[CH:21][CH:20]=[N:19]2)=[C:11]([C:9]([N:4]2[CH2:5][CH2:6][CH2:7][CH2:8][CH:3]2[C:1]#[C:2][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:10])[CH:16]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of (2-ethynylpiperidin-1-yl)[5-methyl-2-(2H-1,2,3-triazol-2-yl)phenyl]methanone (25 mg, 0.085 mmol), bromobenzene (25 mg, 0.15 mmol), CuI (4.9 mg, 0.025 mmol), and triethylamine (0.15 mL, 1.1 mmol) in DMF (0.5 mL) was purged subsurface with nitrogen. Palladium tetrakis (9.8 mg, 0.0085 mmol) was added and the reaction was heated at 90° C. overnight. The reaction was stirred over excess Quadrapure TU overnight, then filtered and dried. The residue was subjected to purification via reverse phase HPLC to provide the title compound which gave a high resolution mass spectrum (ES+) m/z of 371.1872, calculated for M+H+ [C23H22N4O: 371.1866].

Workup

filtrationfiltered
customdried
customThe residue was subjected to purification via reverse phase HPLC

Sources & evidence

ORD record: ord-44e01fca5fb542d5949f5482f598664c
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08940898B2

Reaction notes

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