1H-Indole-4-boronic acid → HCID 60196655, compound

HRID 2169628Notes

Reaction equation

HRID 2169628 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH2:12][C:13]3[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=3)[C:16]#[N:17])[CH2:7][CH:6]3[CH2:21][O:22][CH2:23][CH2:24][N:5]3[C:4]=2[N:3]=1.[NH:25]1[C:33]2[C:28](=[C:29](B(O)O)[CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]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:25]1[C:33]2[C:28](=[C:29]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH2:12][C:13]5[CH:14]=[C:15]([CH:18]=[CH:19][CH:20]=5)[C:16]#[N:17])[CH2:7][CH:6]5[CH2:21][O:22][CH2:23][CH2:24][N:5]5[C:4]=4[N:3]=3)[CH:30]=[CH:31][CH:32]=2)[CH:27]=[CH:26]1

Participants

6

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 86670152HCID 86670152, compound

Product 1

HCID 60196655HCID 60196655, 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 3 using 3-((2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)methyl)benzonitrile (PREPARATION x14, 59 mg, 0.173 mmol), PdCl2(dppf) (6.32 mg, 8.63 μmol) and 1H-indol-4-ylboronic acid (55.6 mg, 0.345 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.16-3.32 (m, 3 H), 3.55-3.66 (m, 2 H), 3.92-4.06 (m, 2 H), 4.07-4.16 (m, 1 H), 4.57-4.78 (m, 3 H), 6.96-7.07 (m, 1 H), 7.20-7.32 (m, 1 H), 7.40-7.48 (m, 1 H), 7.52-7.69 (m, 4 H), 7.71-7.84 (m, 2 H), 7.85-7.93 (m, 1 H), 11.45-11.59 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C25H22N6O, 423.19; found 423.3.

Sources & evidence

ORD record
ord-46a1c23d3e2b4b9f9e0adc1db548c0ed
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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