Triethylamine → HCID 22100392, compound

HRID 1457776Notes

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].[C:26]1(OB(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C>CN(C)C=O.C(OCC)(=O)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]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH:3]=[C:4]2[N:12]=1)[CH2:14][CH2:15][CH3:16]

Participants

Conditions

Temperature: 120 °C

Procedure

4.8 g(0.01197 mole) of the compound obtained in step 7, 3.75 g(0.03591 mole) of phenylboric acid, 0.2 g(0.0012 mole) of palladium acetate, 0.46 g(0.0024 mole) of triphenylphosphine and 8.9 ml(0.0838 mole) of triethylamine were dissolved in 20 ml of dimethyl formamide. The reaction solution was stirred for 3 hours at 120° C., diluted with 100 ml of ethyl acetate and washed with water(50 ml×3). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The residue was purified with column chromatography(5% MeOH in CH2 Cl2) to obtain 4.57 g of the title compound(yield 96%).

Workup

washwashed with water(50 ml×3)
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated under reduced pressure
customThe residue was purified with column chromatography(5% MeOH in CH2 Cl2)

Sources & evidence

ORD record: ord-042b61e4903a440a881375806dd2a269
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05849753

Reaction notes

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