Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate → tert-butyl 3-((4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)azetidine-1-carboxylate

HRID 2274782Notes

Reaction equation

HRID 2274782 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH:26]4[CH2:31]CN(C(OC(C)(C)C)=O)CC4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.FC1C=C2C(C(C3C=NNC=3)=CN2S(C2C=CC=CC=2)(=O)=O)=CC=1.CS(OCC1C[N:71]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:70]1)(=O)=O>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH:26]4[CH2:31][N:71]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[CH2:70]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylateHCID 1180601346-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole2×HCID 118060320tert-butyl 4-((4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 118060745tert-butyl 3-((4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)azetidine-1-carboxylateYield 76%

Procedure

Following the general method as outlined in Intermediate 20, starting from 6-fluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole (Intermediate 5; 1.22 g; 3.56 mmol) and tert-butyl 3-(((methylsulfonyl)oxy)methyl)azetidine-1-carboxylate (1.40 g; 5.28 mmol), 1.37 g (76%) of the title compound as a yellow solid.

Sources & evidence

ORD record
ord-b801877ca4b74b73bfa304c35134f3ae
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

Loading…