1H-Indole-4-boronic acid → 2-(1H-indol-4-yl)-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169634Notes

Reaction equation

HRID 2169634 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=3)[CH2:7][CH:6]3[CH2:20][O:21][CH2:22][CH2:23][N:5]3[C:4]=2[N:3]=1.[NH:24]1[C:32]2[C:27](=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25]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]>[NH:24]1[C:32]2[C:27](=[C:28]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH2:12][C:13]5[CH:18]=[CH:17][CH:16]=[C:15]([CH3:19])[N:14]=5)[CH2:7][CH:6]5[CH2:20][O:21][CH2:22][CH2:23][N:5]5[C:4]=4[N:3]=3)[CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25]1

Participants

6

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 86670105HCID 86670105, compound

Product 1

HCID 601973752-(1H-indol-4-yl)-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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 3 using 2-chloro-5-((6-methylpyridin-2-yl)methyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x28, 36 mg, 0.108 mmol), 1H-indol-4-ylboronic acid (34.9 mg, 0.217 mmol) and PdCl2(dppf) (7.94 mg, 10.85 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.50 (s, 3 H), 3.26-3.44 (m, 3 H), 3.54-3.68 (m, 2 H), 3.95-4.06 (m, 1 H), 4.06-4.17 (m, 1 H), 4.55-4.81 (m, 4 H), 6.93-7.05 (m, 1 H), 7.20-7.37 (m, 3 H), 7.54-7.64 (m, 3 H), 7.64-7.70 (m, 1 H), 7.70-7.81 (m, 1 H), 11.47-11.66 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O, 412.20; found 412.3.

Sources & evidence

ORD record
ord-d7a701e5bc384c9398143c9bf82ee736
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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