5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridine → HCID 60198095, compound

HRID 1631787Notes

Reaction equation

HRID 1631787 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]([S:19]([CH3:22])(=[O:21])=[O: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:36]=[C:37]3[CH:43]=[CH:42][NH:41][C:38]3=[N:39][CH:40]=2)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]>[CH3:22][S:19]([C:16]1[CH:17]=[CH:18][C:13]([CH2:12][N:8]2[CH2:7][CH:6]3[CH2:23][O:24][CH2:25][CH2:26][N:5]3[C:4]3[N:3]=[C:2]([C:35]4[CH:36]=[C:37]5[CH:43]=[CH:42][NH:41][C:38]5=[N:39][CH:40]=4)[N:11]=[CH:10][C:9]2=3)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 2

HCID 242087895-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(2,3-b)pyridineHCID 866700922-Chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 60198095HCID 60198095, 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 2-chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine (PREPARATION x9, 50 mg, 0.127 mmol), 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (61.8 mg, 0.253 mmol) and PdCl2(dppf) (4.63 mg, 6.33 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.14-3.26 (m, 2H), 3.31-3.45 (m, 6H), 3.54-3.65 (m, 2H), 3.93-4.03 (m, 1H), 4.03-4.13 (m, 1H), 4.62-4.72 (m, 2H), 6.51-6.61 (m, 1H), 7.44-7.53 (m, 1H), 7.53-7.60 (m, 1H), 7.60-7.68 (m, 2H), 7.89-7.96 (m, 2H), 8.67-8.73 (m, 1H), 8.99-9.07 (m, 1H), 11.76-12.07 (m, 1H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16. found 477.3.

Sources & evidence

ORD record
ord-0d3dceae9fe744e69059ec278274d8c1
Source dataset
uspto-grants-2014_07
Patent number
US08791107B2

Reaction notes

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