Benzamide → HCID 68577075, compound

HRID 1949051Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([NH:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16]C=1OC)[CH:6]=[CH:5]2.[C:22]([NH2:30])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])[O-:32].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C3OC4C(=CC=CC=4P(C4C=CC=CC=4)C4C=CC=CC=4)C(C)(C)C=3C=CC=2)C=CC=CC=1>O1CCOCC1>[CH3:16][C:17]1[O:32][C:14]([CH2:13][NH:12][C:7]2[CH:6]=[CH:5][C:4]3[C:9](=[CH:10][CH:11]=[C:2]([NH:30][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH:3]=3)[N:8]=2)=[CH:19][CH:18]=1

Participants

Conditions

Temperature: 100 °C

Procedure

(6-Bromo-quinolin-2-yl)-(5-methyl-furan-2-ylmethyl)-amine (prepared from 6-bromo-2-chloroquinoline and 5-methyl-2-furanmethanamine as described in example 43, step A, 200 mg, 0.631 mmol) was dissolved in 5 mL dioxane. Argon was bubbled through the solution for 2 minutes to remove oxygen. Benzamide (107 mg, 0.884 mmol), cesium carbonate (308 mg, 0.948 mmol) bis(dibenzylideneacetone)palladium (29 mg, 0.032 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (55 mg, 0.095 mmol) were added. The reaction mixture was stirred in a sealed tube at 100° C. for 16 h. The solvent was evaporated and the residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->60:40 gradient). The title compound was obtained as a white solid (110 mg, 49%), MS: m/e=358.3 (M+H+).

Workup

customArgon was bubbled through the solution for 2 minutes
customto remove oxygen
customThe solvent was evaporated
customthe residue purified by flash chromatography on silica gel (heptane/ethyl acetate 100:0->60:40 gradient)

Sources & evidence

ORD record: ord-72138ca8fb00495fad6dc46213e483ea
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08399674B2

Reaction notes

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