1H-Indole-4-boronic acid → (R)-4-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)cyclohexanol

HRID 1631807Notes

Reaction equation

HRID 1631807 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH:12]3[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]3)[CH2:7][C@@H:6]3[CH2:19][O:20][CH2:21][CH2:22][N:5]3[C:4]=2[N:3]=1.[NH:23]1[C:31]2[C:26](=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]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:23]1[C:31]2[C:26](=[C:27]([C:2]3[N:11]=[CH:10][C:9]4[N:8]([CH:12]5[CH2:17][CH2:16][CH:15]([OH:18])[CH2:14][CH2:13]5)[CH2:7][C@@H:6]5[CH2:19][O:20][CH2:21][CH2:22][N:5]5[C:4]=4[N:3]=3)[CH:28]=[CH:29][CH:30]=2)[CH:25]=[CH:24]1

Participants

6

Reactant 2

HCID 27631731H-Indole-4-boronic acidHCID 86670131HCID 86670131, compound

Product 1

HCID 68195285(R)-4-(2-(1H-indol-4-yl)-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)cyclohexanol

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 (R)-4-(2-chloro-6a,7,9,10-tetrahydro-[1,4]oxazino[3,4-h]pteridin-5(6H)-yl)cyclohexanol (PREPARATION x63, 30 mg, 0.092 mmol), 1H-indol-4-ylboronic acid (71.9 mg, 0.447 mmol) and PdCl2(dppf) (8.17 mg, 0.011 mmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL) (2 mg, 5%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.32-1.85 (m, 6H), 2.78-2.93 (m, 1H), 2.96-3.11 (m, 1H), 3.50-3.75 (m, 6H), 3.81-3.90 (m, 2H), 3.94-4.10 (m, 1H), 4.36-4.45 (m, 1H), 4.49-4.60 (m, 1H), 6.51-6.62 (m, 1H), 7.02-7.19 (m, 1H), 7.27-7.45 (m, 3H), 7.80-7.98 (m, 2H), 11.04-11.16 (m, 1H); ESI-MS m/z [M+H]+ calc'd for C23H27N5O2, 406.22. found 406.4.

Sources & evidence

ORD record
ord-7492688fbadc45fda15c8e3cf9915966
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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