Triphenylphosphine → 1-({5-Chloro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine

HRID 1500930Notes

Reaction equation

HRID 1500930 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([CH2:17]O)=[CH:5]2.[CH3:19][S:20]([C:23]1[C:31]2[C:26](=[CH:27][N:28]=[CH:29][CH:30]=2)[NH:25][N:24]=1)(=[O:22])=[O:21].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][CH2:12][S:13]([CH3:16])(=[O:15])=[O:14])[C:6]([CH2:17][N:25]1[C:26]3=[CH:27][N:28]=[CH:29][CH:30]=[C:31]3[C:23]([S:20]([CH3:19])(=[O:21])=[O:22])=[N:24]1)=[CH:5]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89924301[5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanolHCID 178504858HCID 178504858, compound

Product 1

HCID 729487211-({5-Chloro-1-[2-(methylsulfonyl)ethyl]-1H-indol-2-yl}methyl)-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridineYield 2.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [5-chloro-1-(2-methanesulfonyl-ethyl)-1H-indol-2-yl]-methanol (287 mg, 1.0 mmol), 3-methanesulfonyl-1H-pyrazolo[3,4-c]pyridine (197 mg, 1.0 mmol) and PPh3 (786 mg, 3 mmol) in THF (50 mL) was added DIAD (606 mg, 3 mmol) dropwise in an ice-water bath under N2 protection. The mixture then stirred at RT overnight. The reaction was purified by preparative-HPLC to give the title product (13.5 mg, 2.8%).

Workup

  1. customThe reaction was purified by preparative-HPLC

Sources & evidence

ORD record
ord-173b93d9c971490db4f617007a1aae11
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

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