Pivalic acid → HCID 67208614, compound

HRID 579187Notes

Reaction equation

[CH3:1][O:2][C:3]([C:5]1[S:6][CH:7]=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH:11]1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:4].Br[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+].F[B-](F)(F)F.C(O)(=O)C(C)(C)C>CC([O-])=O.CC([O-])=O.[Pd+2].CC(N(C)C)=O>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:24]2[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=2)=[CH:8][C:9]=1[N:10]1[C:15](=[O:16])[CH2:14][CH2:13][CH2:12][CH:11]1[CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)=[O:4]

Participants

Conditions

Temperature: 100 °C

Procedure

A 5 mL vial was charged with 3-(2-cyclohexyl-6-oxo-piperidin-1-yl)-thiophene-2-carboxylic acid methyl ester (32 mg, 0.10 mmol, 1.0 equiv), 1-bromo-4-fluoro benzene (17 mg, 0.10 mmol, 1.0 equiv), potassium carbonate (20.6 mg, 0.15 mmol, 1.5 equiv), tricyclophenylphosphine tetrafluoroborate (8.7 mg, 0.024 mmol, 0.24 equiv), Pd(OAc)2 (2.7 mg, 0.012 mmol, 0.12 equiv), pivalic acid (6.1 mg, 0.060 mmol, 0.6 equiv) and DMA (0.3 mL). The resulted mixture was flushed with nitrogen and stirred at 100° C. for 18 hours. The mixture was loaded to silica gel column and flushed with EtOAc/heptane 67% to give product 27 mg (yield 65%).

Workup

customThe resulted mixture was flushed with nitrogen
customflushed with EtOAc/heptane 67%

Sources & evidence

ORD record: ord-5dfb4bd64dc44fbb8db4143611181a56
Source dataset: uspto-grants-2015_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09040690B2

Reaction notes

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