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

HRID 2169621Notes

Reaction equation

HRID 2169621 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH2:7][CH:6]3[CH2:22][O:23][CH2:24][CH2:25][N:5]3[C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:42]=[CH:41][CH:40]=[C:39]3[C:35]=2[CH:36]=[CH:37][NH:38]3)O1>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:38]1[C:39]2[C:35](=[C:34]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([S:12]([C:15]5[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=5)(=[O:14])=[O:13])[CH2:7][CH:6]5[CH2:22][O:23][CH2:24][CH2:25][N:5]5[C:4]=4[N:3]=3)[CH:42]=[CH:41][CH:40]=2)[CH:36]=[CH:37]1

Participants

6

Reactant 2

HCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 866700942-Chloro-5-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 601977662-(1H-indol-4-yl)-5-tosyl-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-tosyl-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x11, 68 mg, 0.179 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (87 mg, 0.357 mmol) and PdCl2(dppf) (6.53 mg, 8.93 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 2.35-2.41 (m, 3 H), 2.55-2.66 (m, 1 H), 2.68-2.76 (m, 1 H), 2.97-3.09 (m, 1 H), 3.17-3.27 (m, 1 H), 3.82-3.98 (m, 2 H), 4.16-4.27 (m, 1 H), 4.53-4.63 (m, 1 H), 4.57-4.57 (m, 1 H), 7.14-7.24 (m, 1 H), 7.23-7.31 (m, 1 H), 7.38-7.50 (m, 3 H), 7.51-7.63 (m, 3 H), 8.00-8.10 (m, 1 H), 8.48-8.58 (m, 1 H), 11.19-11.35 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H23N5O3S, 462.15; found 462.4.

Sources & evidence

ORD record
ord-e6fd46a3141045128cb492970637514e
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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