Potassium Carbonate → 4-Benzyloxy-3-cyclopropyl-1-cyclopropylmethyl-1H-pyridin-2-one

HRID 516630Notes

Reaction equation

C([O-])(O)=O.[Na+].[CH:6]1(B(O)O)[CH2:8][CH2:7]1.C(=O)([O-])[O-].[K+].[K+].[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1I)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O1CCOCC1>[CH2:18]([O:25][C:26]1[CH:31]=[CH:30][N:29]([CH2:32][CH:33]2[CH2:35][CH2:34]2)[C:28](=[O:36])[C:27]=1[CH:6]1[CH2:8][CH2:7]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 175 °C

Procedure

NaHCO3 (1.0 g, excess), cyclopropylboronic acid (0.74 g, 8.93 mmol), potassium carbonate (1.23 g, 8.93 mmol) and [1,1′-bis(diphenylphosphino)ferrocene] dichloropalladium(II)-DCM complex (0.36 g, 0.45 mmol) were added to a solution of intermediate D10 (1.0 g, 2.98 mmol) in 1,4-dioxane (10 ml). The resulting mixture was heated at 175° C. for 20 minutes under microwave irradiation, after which it was filtered through diatomaceous earth and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent). The desired fractions were collected and evaporated in vacuo yielding D34 (0.6 g, 69%).

Workup

filtrationafter which it was filtered through diatomaceous earth
customthe solvent was evaporated in vacuo
customThe crude residue was purified by column chromatography (silica gel; 0-3% methanol/DCM as eluent)
customThe desired fractions were collected
customevaporated in vacuo
customyielding D34 (0.6 g, 69%)

Sources & evidence

ORD record: ord-845de4cedd0046eaa462aadd49d1e39e
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09114138B2

Reaction notes

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