(1-Acetyl-1H-pyrrolo[2,3-c]pyridin-4-yl)boronic acid → 5-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[2,3-c]pyridin-4-yl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

HRID 2169625Notes

Reaction equation

HRID 2169625 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.C([N:30]1[C:34]2=[CH:35][N:36]=[CH:37][C:38](B(O)O)=[C:33]2[CH:32]=[CH:31]1)(=O)C>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:38]4[CH:37]=[N:36][CH:35]=[C:34]5[NH:30][CH:31]=[CH:32][C:33]=45)[N:11]=[CH:10][C:9]2=3)=[CH:14][CH:15]=1)(=[O:21])=[O:20]

Participants

6

Reactant 2

HCID 68195100(1-Acetyl-1H-pyrrolo[2,3-c]pyridin-4-yl)boronic acidHCID 866700922-Chloro-5-(4-(methylsulfonyl)benzyl)-5,6,6a,7,9,10-hexahydro-[1,4]oxazino[3,4-h]pteridine

Product 1

HCID 601979875-(4-(methylsulfonyl)benzyl)-2-(1H-pyrrolo[2,3-c]pyridin-4-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, 75 mg, 0.190 mmol), 1-acetyl-1H-pyrrolo[2,3-c]pyridin-4-ylboronic acid (77 mg, 0.380 mmol) and PdCl2(dppf) (6.95 mg, 9.50 μmol) in dioxane (2 mL) and aqueous saturated NaHCO3 (0.4 mL). 1H NMR (400 MHz, DMSO-d6) δ 3.08-3.19 (m, 1 H), 3.21 (m, 2 H), 3.23-3.34 (m, 2 H), 3.47-3.56 (m, 1 H), 3.57-3.67 (m, 1 H), 3.70-3.81 (m, 1 H), 3.93-4.01 (m, 2 H), 4.06-4.15 (m, 1 H), 4.49-4.58 (m, 1 H), 4.64-4.80 (m, 2 H), 7.55-7.68 (m, 3 H), 7.69-7.75 (m, 1 H), 7.88-7.98 (m, 2 H), 8.28-8.37 (m, 1 H), 8.86-8.96 (m, 1 H), 9.05-9.15 (m, 1 H), 12.85-12.97 (m, 1 H). ESI-MS m/z [M+H]+ calc'd for C24H24N6O3S, 477.16; found 477.5.

Sources & evidence

ORD record
ord-5269046704f24898a723746cfb6eaeb8
Source dataset
uspto-grants-2015_06
Patent number
US09045496B2

Reaction notes

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