Potassium Hydroxide → HCID 89526503, compound

HRID 588096Notes

Reaction equation

[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9](C(O)=O)=[CH:10][C:5]=2[N:4]([C:14]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[N:3]=1.C1(P([N:47]=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[OH-].[K+]>O1CCOCC1>[Br:1][C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:47])=[CH:10][C:5]=2[N:4]([C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:3]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a suspension of 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridine-6-carboxylic acid (1.95 g, 4.03 mmol) and diphenylphosphoryl azide (1.047 mL, 4.83 mmol) in 1,4-dioxane (19.50 mL) was added a mixture of TEA (0.842 mL, 6.04 mmol) in 1,4-dioxane (10 mL) drop-wise over 5 min. The reaction mixture was heated to 80° C. for 2 h. A solution of KOH (1 N, 20.13 mL, 20.13 mmol) was added at 80° C. The reaction mixture was stirred overnight. Room temperature was obtained and the reaction mixture was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (50% EtOAc/hexanes) to give 3-bromo-1-trityl-1H-pyrazolo[4,3-c]pyridin-6-amine MS ESI calc'd. for C25H20BrN4 [M+H]+ 455. found 455.

Workup

additionwas added
customRoom temperature was obtained
extractionthe reaction mixture was extracted with EtOAc
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-e02a59da07714e899a9220de5f294dec
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226922B2

Reaction notes

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