Triphenylphosphine → HCID 72948898, compound

HRID 1500935Notes

Reaction equation

HRID 1500935 reaction equation
CS(O[CH2:6][C:7]1[N:8]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:22])=[O:21])[C:9]2[C:14]([CH:15]=1)=[CH:13][C:12]([Cl:16])=[CH:11][CH:10]=2)(=O)=O.[CH3:24][S:25]([C:28]1[C:36]2[C:31](=[CH:32][N:33]=[CH:34][CH:35]=2)[NH:30][N:29]=1)(=[O:27])=[O:26].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:16][C:12]1[CH:13]=[C:14]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:17][CH2:18][CH2:19][S:20]([CH3:23])(=[O:21])=[O:22])[C:7]([CH2:6][N:30]1[C:31]3=[CH:32][N:33]=[CH:34][CH:35]=[C:36]3[C:28]([S:25]([CH3:24])(=[O:26])=[O:27])=[N:29]1)=[CH:15]2

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 89924349HCID 89924349, compoundHCID 178504858HCID 178504858, compound

Product 1

HCID 72948898HCID 72948898, compoundYield 19.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of {5-chloro-1-[3-(methylsulfonyl)propyl]-1H-indol-2-yl}methyl methanesulfonate (363 mg, 1.0 mmol), 3-methanesulfonyl-1H-pyrazolo[3,4-c]pyridine (197 mg, 1.0 mmol) and PPh3 (786 mg, 3.0 mmol) in 50 mL of THF was added DIAD (606 mg, 3.0 mmol) dropwise via an additional funnel in an ice-water bath under N2 protection. The mixture was then stirred at RT overnight and then concentrated in vacuo. The residue was purified by preparative-HPLC to give the title product (13.592 mg, yield: 19.2%).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe residue was purified by preparative-HPLC

Sources & evidence

ORD record
ord-54d3876a801d4972a88aa6170bca6f85
Source dataset
uspto-grants-2015_12
Patent number
US09206191B2

Reaction notes

Loading…