Tributylphosphine → 4-[(5-chlorothiophen-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-one

HRID 1497369Notes

Reaction equation

HRID 1497369 reaction equation
[CH:1]1([N:4]2[C:12]([CH3:13])=[C:11]3[C:6]([CH:7]=[CH:8][C:9]([N:14]4[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][C:15]4=[O:21])=[CH:10]3)=[N:5]2)[CH2:3][CH2:2]1.[Cl:22][C:23]1[S:27][C:26]([CH2:28]O)=[CH:25][CH:24]=1.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>O1CCCC1>[Cl:22][C:23]1[S:27][C:26]([CH2:28][O:20][C:17]2[CH:18]=[CH:19][N:14]([C:9]3[CH:8]=[CH:7][C:6]4[C:11](=[C:12]([CH3:13])[N:4]([CH:1]5[CH2:2][CH2:3]5)[N:5]=4)[CH:10]=3)[C:15](=[O:21])[CH:16]=2)=[CH:25][CH:24]=1

Participants

6

Reactant 4

HCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 12554178(5-Chlorothiophen-2-yl)methanolHCID 1177986831-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one

Product 1

HCID 1177986234-[(5-chlorothiophen-2-yl)methoxy]-1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)pyridin-2(1H)-oneYield 20.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-cyclopropyl-3-methyl-2H-indazol-5-yl)-4-hydroxypyridin-2(1H)-one (70 mg) in tetrahydrofuran (5 ml) were added (5-chlorothiophen-2-yl)methanol (74 mg), 1,1′-(azodicarbonyl)dipiperidine (188 mg) and tributylphosphine (151 mg) at room temperature, and the mixture was stirred at the same temperature for 3 hr. The reaction mixture was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (21 mg).

Workup

  1. customThe reaction mixture was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-f5eb3606e81049b28d85202723ee367b
Source dataset
uspto-grants-2015_12
Patent number
US09199963B2

Reaction notes

Loading…