Dimethylformamide → HCID 86722706, compound

HRID 1480492Notes

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21](Br)[CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:30][N:31](C=O)C>[C-]#N.[Zn+2].[C-]#N.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>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][CH2:18][C:19]2[CH:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH:22]=[C:21]([C:30]#[N:31])[CH:20]=2)=[O:16])[CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 150 °C

Procedure

3-Bromo-5-(trifluoromethyl)benzyl 4-((tert-butoxycarbonyl)amino)piperidine-1-carboxylate (Example 63, step 2) (214 mg, 0.445 mmol), zinc cyanide (26.1 mg, 0.222 mmol) and Pd(PPh3)4 (20.5 mg, 0.018 mmol) were dissolved in DMF (4 ml) and the vial flushed with nitrogen. The mixture was heated in the microwave at 150° C. for 10 mins, then cooled and diluted with EtOAc (30 ml). This was washed with a saturated solution of brine, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by chromatography on a 4 g silica column using 0-50% EtOAC/hexanes as eluent gave the title compound.

Workup

customthe vial flushed with nitrogen
temperaturecooled
additiondiluted with EtOAc (30 ml)
washThis was washed with a saturated solution of brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customPurification by chromatography on a 4 g silica column

Sources & evidence

ORD record: ord-ef220dac0f844420ba7d0b841309b829
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409895B2

Reaction notes

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