1,4-Dioxane → HCID 68195078, compound

HRID 1631771Notes

Reaction equation

HRID 1631771 reaction equation
Cl[C:2]1[N:11]=[CH:10][C:9]2[NH:8][CH2:7][CH:6]3[CH2:12][O:13][CH2:14][CH2:15][N:5]3[C:4]=2[N:3]=1.CO[C:18]1[CH:26]=[C:25]2[C:21]([C:22](B3OC(C)(C)C(C)(C)O3)=[CH:23][N:24]2[C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[CH:20][CH:19]=1.[O:43]1CCOC[CH2:44]1>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]>[N:3]1[C:4]2[N:5]3[CH2:15][CH2:14][O:13][CH2:12][CH:6]3[CH2:7][NH:8][C:9]=2[CH:10]=[N:11][C:2]=1[C:22]1[C:21]2[C:25](=[C:26]([O:43][CH3:44])[CH:18]=[CH:19][CH:20]=2)[N:24]([C:27]([O:29][C:30]([CH3:31])([CH3:32])[CH3:33])=[O:28])[CH:23]=1

Participants

6

Reactant 3

HCID 312751,4-DioxaneHCID 53217219tert-Butyl 6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylateHCID 86670087HCID 86670087, compound

Product 1

HCID 68195078HCID 68195078, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 516892Sodium BicarbonateSolvent

Procedure

The title compound was prepared in a manner similar to EXAMPLE 1 using 2-chloro-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x2, 50 mg, 0.221 mmol), tert-butyl 6-methoxy-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole-1-carboxylate (124 mg, 0.331 mmol) and PdCl2(dppf) (12.91 mg, 0.018 mmol) in dioxane (1.9 mL) and aqueous saturated NaHCO3 (0.4 mL).

Sources & evidence

ORD record
ord-d816a4bdd05d4ff98fca28c28bf7d030
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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