Diisopropylethylamine → HCID 67041981, compound

HRID 716886Notes

Reaction equation

[F:1][C:2]([F:16])([F:15])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][NH:12][CH2:11][CH2:10]2)=[CH:5][CH:4]=1.Br[C:18]1[C:19]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[N:20][C:21]2[C:26]([N:27]=1)=[CH:25][C:24]([C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=2.CCN(C(C)C)C(C)C>CN(C=O)C>[C:32]1([C:19]2[C:18]([N:12]3[CH2:11][CH2:10][CH:9]([C:6]4[CH:5]=[CH:4][C:3]([C:2]([F:1])([F:15])[F:16])=[CH:8][CH:7]=4)[CH2:14][CH2:13]3)=[N:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:28]([O:30][CH3:31])=[O:29])[CH:25]=3)[N:20]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A solution of 4-(4-(trifluoromethyl)phenyl)piperidine (200 mg, 0.87 mmol, 2.00 equiv), methyl 3-bromo-2-phenylquinoxaline-6-carboxylate (150 mg, 0.44 mmol, 1.00 equiv), and DIEA (169 mg, 1.31 mmol, 3.00 equiv) in DMF (10 mL) was placed in a 20-mL sealed tube and stirred overnight at 100° C. in an oil bath. The resulting mixture was concentrated under vacuum and purified via silica gel column (ethyl acetate/petroleum ether (1:20)), yielding 180 mg (84%) of methyl 2-phenyl-3-(4-(4-(trifluoromethyl)phenyl)piperidin-1-yl)quinoxaline-6-carboxylate as a yellow solid.

Workup

customsealed tube
concentrationThe resulting mixture was concentrated under vacuum
custompurified via silica gel column (ethyl acetate/petroleum ether (1:20))

Sources & evidence

ORD record: ord-04b3298530db444598571509ef556dd2
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193693B2

Reaction notes

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