Cesium carbonate → HCID 70978622, compound

HRID 1485460Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][C@@H:13]([CH3:15])[C:12]3=[N:16][N:17]=[C:18]([CH3:19])[N:11]3[C:10]3[CH:20]=[CH:21][C:22](B4OC(C)(C)C(C)(C)O4)=[CH:23][C:9]2=3)=[N:6][CH:7]=1.Br[C:34]1[N:35]=[CH:36][C:37]([NH2:40])=[N:38][CH:39]=1.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH2:14][C@@H:13]([CH3:15])[C:12]3=[N:16][N:17]=[C:18]([CH3:19])[N:11]3[C:10]3[CH:20]=[CH:21][C:22]([C:34]4[N:35]=[CH:36][C:37]([NH2:40])=[N:38][CH:39]=4)=[CH:23][C:9]2=3)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 130 °C

Procedure

To a solution of (R)-6-(5-chloropyridin-2-yl)-1,4-dimethyl-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepine in 1,4-dioxane/H2O (10:1, 5 mL) were added 5-bromopyrazin-2-amine (69.33 mg, 0.40 mmol), Cs2CO3 (197.3 mg, 0.61 mmol) and Tetrakis(triphenylphosphine)palladium(0) (24.1 mg, 0.033 mmol). The mixture was purged with N2 and stirred in the microwave at 130° C. for 20 min. The reaction solution was concentrated and purified by prep-TLC (elute: DCM:CH3OH=15:1) to give (R)-5-(6-(5-chloropyridin-2-yl)-1,4-dimethyl-5,6-dihydro-4H-benzo[b][1,2,4]triazolo[4,3-d][1,4]diazepin-8-yl)pyrazin-2-amine (110 mg, 59%).

Workup

customThe mixture was purged with N2
concentrationThe reaction solution was concentrated
custompurified by prep-TLC (elute: DCM:CH3OH=15:1)

Sources & evidence

ORD record: ord-6b17a4f159f643d7873db2fcc5b59a20
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422292B2

Reaction notes

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