Methanol → HCID 86709421, compound

HRID 882252Notes

Reaction equation

[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10](Br)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[N:17]=[CH:18][C:19]([C:22]#[N:23])=[N:20][CH:21]=2)[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2].[CH3:25][O:26][C:27]([C:29]1[N:34]=[CH:33][C:32](B(O)O)=[CH:31][CH:30]=1)=[O:28].C(N(CC)CC)C.CO>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].COCCOC>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([C:32]3[CH:31]=[CH:30][C:29]([C:27]([O:26][CH3:25])=[O:28])=[N:34][CH:33]=3)=[CH:11][CH:12]=2)[C@H:7]([NH:15][C:16]2[CH:21]=[N:20][C:19]([C:22]#[N:23])=[CH:18][N:17]=2)[CH2:6][C@@H:5]1[CH3:24])(=[O:3])[CH3:2]

Participants

Conditions

Temperature: 120 °C

Procedure

5-(((2S,4R)-1-acetyl-6-bromo-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl)amino)pyrazine-2-carbonitrile (for a preparation, see Intermediate 51) (390 mg, 1.010 mmol), (6-(methoxycarbonyl)pyridin-3-yl)boronic acid (219 mg, 1.21 mmol), PdCl2(dppf) (111 mg, 0.151 mmol) and triethylamine (0.281 ml, 2.02 mmol) were combined in a mixture of dry MeOH (6 mL) and DME (1 mL). The mixture was heated under microwave irradiation to 120° C. for 45 mins. The mixture was then concentrated in vacuo and the residue purified by chromatography (100 g column, EtOAc/cyclohexane gradient) to give methyl 5-((2S,4R)-1-acetyl-4-((5-cyanopyrazin-2-yl)amino)-2-methyl-1,2,3,4-tetrahydroquinolin-6-yl)picolinate (389 mg, 0.879 mmol, 87% yield) as a pink solid.

Workup

concentrationThe mixture was then concentrated in vacuo
customthe residue purified by chromatography (100 g column, EtOAc/cyclohexane gradient)

Sources & evidence

ORD record: ord-807225cb182a41faa98fa628368f2268
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08993554B2

Reaction notes

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