Potassium Carbonate → HCID 57551737, compound

HRID 907288Notes

Reaction equation

[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8](B3OC(C)(C)C(C)(C)O3)[CH:7]=2)[CH2:3][CH2:2]1.Br[C:24]1[CH:25]=[C:26]2[C:31](=[CH:32][CH:33]=1)[C:30](=[O:34])[N:29]([CH2:35][CH:36]1[CH2:38][CH2:37]1)[CH:28]=[C:27]2[CH:39]=[O:40].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C.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>[CH:1]1([NH:4][C:5](=[O:22])[C:6]2[CH:11]=[CH:10][C:9]([CH3:12])=[C:8]([C:24]3[CH:25]=[C:26]4[C:31](=[CH:32][CH:33]=3)[C:30](=[O:34])[N:29]([CH2:35][CH:36]3[CH2:38][CH2:37]3)[CH:28]=[C:27]4[CH:39]=[O:40])[CH:7]=2)[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-cyclopropyl-4-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzamide (0.47 g) [prepared as described in US2005020590], the product of step ii) (0.4 g), tetrakis(triphenylphosphine)palladium(0) (0.15 g) and potassium carbonate (0.54 g) in DMF (10 mL) were heated at 80° C. for 5 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organics were dried over magnesium sulphate and evaporated. The residue was purified (SiO2, eluting with 1:1 ethyl acetate: isohexane) to give the sub-title compound (0.2 g).

Workup

customprepared
washwashed with water and brine
dry with materialThe organics were dried over magnesium sulphate
customevaporated
customThe residue was purified
wash(SiO2, eluting with 1:1 ethyl acetate: isohexane)

Sources & evidence

ORD record: ord-1b098d0390254eda9660238529d7100c
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08012979B2

Reaction notes

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