Triphenylphosphine → HCID 72949631, compound

HRID 1500953Notes

Reaction equation

HRID 1500953 reaction equation
[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:7]([C@@H:9](O)[CH3:10])=[N:8][C:4]=2[CH:3]=1.[CH3:20][S:21]([C:24]1[C:32]2[C:27](=[CH:28][N:29]=[CH:30][CH:31]=2)[NH:26][N:25]=1)(=[O:23])=[O:22].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C(Cl)Cl>[Cl:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]([CH2:12][CH2:13][C:14]([F:17])([F:16])[F:15])[C:7]([C@H:9]([N:26]3[C:27]4=[CH:28][N:29]=[CH:30][CH:31]=[C:32]4[C:24]([S:21]([CH3:20])(=[O:22])=[O:23])=[N:25]3)[CH3:10])=[N:8][C:4]=2[CH:3]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 89933262HCID 89933262, compoundHCID 178504858HCID 178504858, compound

Product 1

HCID 72949631HCID 72949631, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (1S)-1-[5-chloro-1-(3,3,3-trifluoropropyl)-1H-benzimidazol-2-yl]ethanol (145 mg, 0.50 mmol) and 3-methanesulfonyl-1H-pyrazolo[3,4-c]pyridine (140 mg, 0.70 mmol) in DCM (15 mL) was added PPh3 (262 mg, 1.0 mmol) and DEAD (170 mg, 1.0 mmol). The mixture was then stirred at room temperature overnight. After the reaction was complete, the mixture was washed by 2 N aqueous solution of NaOH and the organic layer was concentrated in vacuo. The residue was purified by preparative HPLC to afford 1-{(1R)-1-[5-Chloro-1-(3,3,3-trifluoropropyl)-1H-benzimidazol-2-yl]ethyl}-3-(methylsulfonyl)-1H-pyrazolo[3,4-c]pyridine (56.6 mg).

Workup

  1. washthe mixture was washed by 2 N aqueous solution of NaOH
  2. concentrationthe organic layer was concentrated in vacuo
  3. customThe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-cbd7c505280d4a06a71e80d08f18eaab
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…