6-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-b)pyridine → 5-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169626Notes

Reaction equation

HRID 2169626 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[NH:43][CH:42]=[CH: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[NH:43][CH:42]=[CH: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 242292706-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo(3,2-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 601980945-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[3,2-b]pyridin-6-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

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), 6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[3,2-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 3.03-3.18 (m, 1 H), 3.18-3.30 (m, 5 H), 3.73-3.87 (m, 2 H), 3.92-4.19 (m, 3 H), 4.59-4.81 (m, 3 H), 6.76-6.97 (m, 1 H), 7.53-7.77 (m, 2 H), 7.86-8.08 (m, 2 H), 8.14-8.33 (m, 1 H), 8.96-9.20 (m, 1 H), 9.26-9.42 (m, 1 H), 12.40-12.69 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.2.

Sources & evidence

ORD record
ord-787fce41e9824a61a4eaedb4acba89ba
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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