1H-Indole-4-boronic acid, pinacol ester → HCID 60197876, compound

HRID 2169616Notes

Reaction equation

HRID 2169616 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=3)[CH2:7][CH:6]3[CH2:23][O:24][CH2:25][CH2:26][N:5]3[C:4]=2[N:3]=1.CC1(C)C(C)(C)OB([C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH:37]=[CH:38][NH:39]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:39]1[C:40]2[C:36](=[C:35]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH2:12][C:13]5[CH:18]=[CH:17][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[CH:15][CH:14]=5)[CH2:7][CH:6]5[CH2:23][O:24][CH2:25][CH2:26][N:5]5[C:4]=4[N:3]=3)[CH:43]=[CH:42][CH:41]=2)[CH:37]=[CH:38]1

Participants

6

Reactant 2

HCID 113224711H-Indole-4-boronic acid, pinacol esterHCID 88868223HCID 88868223, compound

Product 1

HCID 60197876HCID 60197876, 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 2 using 2-(4-((2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)phenyl)propan-2-ol (PREPARATION x8, 39 mg, 0.104 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (50.6 mg, 0.208 mmol), and PdCl2(dppf) (6.09 mg, 8.32 μmol) in dioxane (8 mL) and aqueous saturated NaHCO3 (2 mL). 1H NMR (400 MHz, DMSO-d6) δ 1.42 (s, 6 H), 3.18 (m, 4 H), 3.58-3.66 (m, 1 H), 3.94-4.04 (m, 2 H), 4.08-4.15 (m, 1 H), 4.56 (s, 2 H), 4.70-4.79 (m, 1 H), 6.99-7.05 (m, 1 H), 7.23-7.37 (m, 3 H), 7.45-7.51 (m, 3 H), 7.58 (s, 1 H), 7.60-7.69 (m, 2 H), 11.45-11.63 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C27H29N5O2, 456.23; found 456.5.

Sources & evidence

ORD record
ord-b34879391c304e7cb0460924defe10bd
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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