Sodium Bicarbonate → (S)-3-((4-(4-(2-methoxypyridin-4-yl)phenyl)piperazin-1-yl)methyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3',2'-e]pyrazin-6(6aH)-one

HRID 69751Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH2:14][C:15]3[CH:24]=[N:23][C:22]4[N:21]5[CH2:25][CH2:26][CH2:27][CH2:28][C@H:20]5[C:19](=[O:29])[NH:18][C:17]=4[CH:16]=3)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36](B(O)O)[CH:35]=[CH:34][N:33]=1.C(=O)(O)[O-].[Na+]>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].C(Cl)Cl.O1CCOCC1>[CH3:30][O:31][C:32]1[CH:37]=[C:36]([C:2]2[CH:3]=[CH:4][C:5]([N:8]3[CH2:9][CH2:10][N:11]([CH2:14][C:15]4[CH:24]=[N:23][C:22]5[N:21]6[CH2:25][CH2:26][CH2:27][CH2:28][C@H:20]6[C:19](=[O:29])[NH:18][C:17]=5[CH:16]=4)[CH2:12][CH2:13]3)=[CH:6][CH:7]=2)[CH:35]=[CH:34][N:33]=1

Participants

Conditions

Temperature: 135 °C

Procedure

(S)-3-((4-(4-bromophenyl)piperazin-1-yl)methyl)-7,8,9,10-tetrahydro-5H-dipyrido[1,2-a:3′,2′-e]pyrazin-6(6aH)-one (0.04 mmol), 2-methoxypyridin-4-ylboronic acid (0.060 mmol), PdCl2(dppf)-CH2Cl2 Adduct (3.27 mg, 4.00 μmol), sodium bicarbonate (0.500 ml, 0.500 mmol), dioxane (Volume: 1 ml) and a stir bar were sealed in a 5 mL microwave vial. The vial was heated to 135° C. for 30 minutes. The aqueous layer was removed from the vial and reaction mixture the filtered into a 1.8 mL HPLC submission vial. The reaction mixture was purified by LCMS to give a yellow solid: [M+H] calc'd for C28H32N6O2, 485; found, 485.

Workup

customThe aqueous layer was removed from the vial and reaction mixture the
filtrationfiltered into a 1.8 mL HPLC submission vial
customThe reaction mixture was purified by LCMS
customto give a yellow solid

Sources & evidence

ORD record: ord-9a37aa762b1649a38fdfd4ccee7686ce
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08822470B2

Reaction notes

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