1H-Indole-4-boronic acid → HCID 60196657, compound

HRID 1631789Notes

Reaction equation

HRID 1631789 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][C:20]=3[F:21])[C:16]#[N:17])[CH2:7][CH:6]3[CH2:22][O:23][CH2:24][CH2:25][N:5]3[C:4]=2[N:3]=1.[NH:26]1[C:34]2[C:29](=[C:30](B(O)O)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]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:26]1[C:34]2[C:29](=[C:30]([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][C:20]=5[F:21])[C:16]#[N:17])[CH2:7][CH:6]5[CH2:22][O:23][CH2:24][CH2:25][N:5]5[C:4]=4[N:3]=3)[CH:31]=[CH:32][CH:33]=2)[CH:28]=[CH:27]1

Participants

6

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 86670153HCID 86670153, compound

Product 1

HCID 60196657HCID 60196657, 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)-4-fluorobenzonitrile (PREPARATION x15, 73 mg, 0.203 mmol), PdCl2(dppf) (7.42 mg, 10.14 μmol) and 1H-indol-4-ylboronic acid (65.3 mg, 0.406 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.18-3.30 (m, 3H), 3.46-3.53 (m, 1H), 3.56-3.67 (m, 1H), 3.92-4.05 (m, 2H), 4.07-4.17 (m, 1H), 4.58-4.78 (m, 3H), 6.98-7.08 (m, 1H), 7.22-7.32 (m, 1H), 7.48-7.60 (m, 3H), 7.60-7.70 (m, 2H), 7.89-8.03 (m, 2H), 11.47-11.58 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C25H21FN6O, 441.18. found 441.3.

Sources & evidence

ORD record
ord-c635eb15fcf6454282676caaadbdbf8f
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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