Triethylamine → HCID 18694281, compound

HRID 1870896Notes

Reaction equation

Br[C:2]1[CH:11]=[CH:10][C:9]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].B([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)(O)O.C(N(CC)CC)C>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:7][O:6][C:4]([C:3]1[CH:8]=[C:9]([N:12]2[CH2:16][CH2:15][CH2:14][C:13]2=[O:17])[CH:10]=[CH:11][C:2]=1[C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

A stirred solution of methyl 2-bromo-5-(2-oxopyrrolidin-1-yl)benzoate (D52, 1.7 g; 5.73 mmol) in DMF (13 ml) was treated with 4-boronobenzoic acid (0.95 g,5.73 mmol) under argon, followed by tetrakis(triphenylphosphine)palladium (O) (104 mg) and triethylamine (2.34 ml, 0.02 mol). After heating for 18 h at 100° C., the reaction mixture was concentrated under reduced pressure and the residue partitioned between 10% aqueous Na2CO3 solution and ethyl acetate. The basic aqueous layer was acidified with 5M HCl acid, precipitating the crude product as a white solid, which was recrystallised from ethanol (137 mg, 7%).

Workup

concentrationthe reaction mixture was concentrated under reduced pressure
customthe residue partitioned between 10% aqueous Na2CO3 solution and ethyl acetate
customprecipitating the crude product as a white solid, which
customwas recrystallised from ethanol (137 mg, 7%)

Sources & evidence

ORD record: ord-d1f56b20ab1a477c9d1472d19e03bd0b
Source dataset: uspto-grants-2000_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06100272

Reaction notes

Loading…