2,3-Methylenedioxyphenyl boronic acid → HCID 68195074, compound

HRID 2169643

Reaction equation

HRID 2169643 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[CH:6]3[CH2:13][O:14][CH2:15][CH2:16][N:5]3[C:4]=2[N:3]=1.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25](B(O)O)[C:20]=2[O:19][CH2:18]1>O1CCOCC1.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]>[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[C:25]([C:2]3[N:11]=[CH:10][C:9]4[NH:8][C:7](=[O:12])[CH:6]5[CH2:13][O:14][CH2:15][CH2:16][N:5]5[C:4]=4[N:3]=3)[C:20]=2[O:19][CH2:18]1

Participants

6

Reactant 2

HCID 41926592,3-Methylenedioxyphenyl boronic acidHCID 86651560HCID 86651560, compound

Product 1

HCID 68195074HCID 68195074, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 84 using 2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-6(5H)-one (PREPARATION x1, 50 mg, 0.208 mmol), benzo[d][1,3]dioxol-4-ylboronic acid (51.7 mg, 0.312 mmol) and PdCl2(dppf) (7.60 mg, 10.39 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.96-3.09 (m, 1 H), 3.62 (m, 2 H), 3.93-4.01 (m, 1 H), 4.11-4.20 (m, 1 H), 4.36-4.46 (m, 1 H), 4.52-4.62 (m, 1 H), 6.12 (s, 2 H), 6.94 (t, 1 H), 7.02 (m, 1 H), 7.58-7.65 (m, 1 H), 7.83 (s, 1 H), 10.98 (s, 1H). ESI-MS m/z [M+H]+ calc'd for C16H14N4O4, 327.10; found 327.3.

Sources & evidence

ORD record
ord-ca9f7a27743b4c6a85f94ee8d9f76d04
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Linked notes

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