HCID 66746146, compound → HCID 68089767, compound

HRID 1961434Notes

Reaction equation

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

Participants

Conditions

Temperature: 140 °C

Procedure

In a screw cap pressure tube were tert-butyl 3-bromo-4-(4,4-dimethylpiperidin-1-yl)benzylcarbamate (105 mg, 0.26 mmol) and CuCN (47.3 mg, 0.53 mmol) suspended in DMF (1.0 ml). N2 was bubbled through the suspension for 5 min. The tube was sealed and the mixture heated to 140° C. overnight. The mixture was allowed to cool and then it was poured over ice-water. FeCl3 (94.3 mg, 0.58 mmol) was added and the product extracted with EtOAc. The combined organic extracts were dried (MgSO4), filtered and concentrated. The crude product was purified by flash chromatography (Pet. Ether/EtOAc 4:1) affording 40 mg (45%) of the title compound.

Workup

customIn a screw cap pressure tube
customN2 was bubbled through the suspension for 5 min
customThe tube was sealed
temperatureto cool
additionit was poured over ice-water
extractionthe product extracted with EtOAc
dry with materialThe combined organic extracts were dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customThe crude product was purified by flash chromatography (Pet. Ether/EtOAc 4:1)

Sources & evidence

ORD record: ord-da6364aaf4b44c8fbd2f19ac50ab9aa6
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08415333B2

Reaction notes

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