Triethylamine → HCID 70208434, compound

HRID 1457786Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[N:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH3:16])[N:10]([CH2:17][C:18](=[O:25])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:5]2=[N:6][C:7]=1[CH2:8][OH:9].[CH:26](OB(O)O)=[CH:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:13]([C:11]1[N:10]([CH2:17][C:18](=[O:25])[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:5]2=[N:6][C:7]([CH2:8][OH:9])=[C:2]([CH:26]=[CH:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH:3]=[C:4]2[N:12]=1)[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 120 °C

Procedure

5.08 g(0.0127 mole) of the compound obtained in step 7 of Example 1 was dissolved in 12 ml of dimethylformamide(DMF) and to the resulting solution were added 5.64 g(0.0381 mole) of styrylboric acid, 0.29 g(0.00127 mole) of palladium acetate, 0.67 g(0.00254 mole) of triphenylphosphine and 13 ml(0.0889 mole) of triethylamine. The resultant was stirred for 1 hour at 120° C., cooled, extracted with 300 ml of ethyl acetate and washed with 300 ml of water. The organic layer was dried over anhydrous magnesium sulfate, concentrated under reduced pressure and purified with column chromatography (methanol/methylene chloride=1:9) to obtain 4.58 g of the title compound(yield 85%).

Workup

temperaturecooled
extractionextracted with 300 ml of ethyl acetate
washwashed with 300 ml of water
dry with materialThe organic layer was dried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
custompurified with column chromatography (methanol/methylene chloride=1:9)

Sources & evidence

ORD record: ord-28d16f2dece4496491871bc94e69381a
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849753

Reaction notes

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