4-fluoro-5-(tributylstannyl)-1H-pyrazole → N-(4-(Chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)-6-(3-hydroxy-3-methylazetidin-1-yl)nicotinamide

HRID 525768Notes

Reaction equation

HRID 525768 reaction equation
[Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16](I)[C:15]([N:19]3[CH2:22][C:21]([OH:24])([CH3:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1.[F:28][C:29]1[CH:30]=[N:31][NH:32][C:33]=1[Sn](CCCC)(CCCC)CCCC>>[Cl:1][C:2]([F:27])([F:26])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[C:16]([C:33]3[NH:32][N:31]=[CH:30][C:29]=3[F:28])[C:15]([N:19]3[CH2:22][C:21]([OH:24])([CH3:23])[CH2:20]3)=[N:14][CH:13]=2)=[CH:6][CH:5]=1

Participants

3

Reactant 2

HCID 111530444-fluoro-5-(tributylstannyl)-1H-pyrazoleHCID 89906632N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxy-3-methylazetidin-1-yl)-5-iodonicotinamide

Product 1

HCID 118044992N-(4-(Chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)-6-(3-hydroxy-3-methylazetidin-1-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Example 92 using N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxy-3-methylazetidin-1-yl)-5-iodonicotinamide (Stage 90.1) and 4-fluoro-5-(tributylstannyl)-1H-pyrazole to afford a white solid. HPLC (Condition 7) tR=5.813 min, UPLC-MS (Condition 8) tR=0.98 min, m/z=468.1 [M+H]+; 1H-NMR (400 MHz, DMSO-d6) δ ppm 1.34 (s, 3H) 3.54-3.74 (m, 4H) 5.49 (s, 1H) 7.34 (d, J=8.60 Hz, 2H) 7.58-7.71+7.94-8.01 (m, 1H) 7.83-7.92 (m, 2H) 8.05 (br. s, 1H) 8.78 (br. s, 1H) 10.23 (s, 1H) 13.03 (br.s, 1H).

Workup

  1. customto afford a white solid

Sources & evidence

ORD record
ord-6292cb22f25e4dd596ef5a5b9b20ceb1
Source dataset
uspto-grants-2016_05
Patent number
US09340537B2

Reaction notes

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