Pivalaldehyde → rac-2-tert-butyl-7-(2-chlorophenyl)-6-(4-chlorophenyl)-2H-pyrano[2,3-b]pyridin-4(3H)-one

HRID 1673204Notes

Reaction equation

[C:1]([C:4]1[C:5](=[O:24])[NH:6][C:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[Cl:23])=[C:8]([C:10]2[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=2)[CH:9]=1)(=[O:3])[CH3:2].[CH:25](=O)[C:26]([CH3:29])([CH3:28])[CH3:27].N1CCCC1>C(#N)C>[C:26]([CH:29]1[O:24][C:5]2=[N:6][C:7]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:23])=[C:8]([C:10]3[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=3)[CH:9]=[C:4]2[C:1](=[O:3])[CH2:2]1)([CH3:28])([CH3:27])[CH3:25]

Participants

Conditions

Temperature: 70 °C

Procedure

To the product of Example 4 Step A (0.75 g, 2.09 mmol) was added pivalaldehyde (2. mL, 20.9 mmol), pyrrolidine (0.26 mL, 3.14 mmol) and acetonitrile (15 mL). The reaction was heated to 70° C. for 19 h. The reaction was then concentrated and the residue was purified directly by flash chromatography on silica gel gradient eluted with 0-35% EtOAc in hexane to afford the title compound. (LC-2) HPLC/MS: 426.3 (M+1), 428.3 (M+3); Rt=4.32 min.

Workup

concentrationThe reaction was then concentrated
customthe residue was purified directly by flash chromatography on silica gel gradient
washeluted with 0-35% EtOAc in hexane

Sources & evidence

ORD record: ord-030d13193c5847d7a08a548ad39b54b1
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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