4-fluoro-5-(tributylstannyl)-1H-pyrazole → 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)nicotinamide

HRID 73789Notes

Reaction equation

HRID 73789 reaction equation
[Cl:1][C:2]1[C:21](I)=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1.[F:23][C:24]1[CH:25]=[N:26][NH:27][C:28]=1[Sn](CCCC)(CCCC)CCCC>>[Cl:1][C:2]1[C:21]([C:28]2[NH:27][N:26]=[CH:25][C:24]=2[F:23])=[CH:20][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][C:16]([Cl:19])([F:18])[F:17])=[CH:11][CH:10]=2)=[O:7])=[CH:4][N:3]=1

Participants

3

Reactant 2

HCID 111530444-fluoro-5-(tributylstannyl)-1H-pyrazoleHCID 867026266-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide

Product 1

HCID 867026256-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-(4-fluoro-1H-pyrazol-5-yl)nicotinamide

Procedure

The title compound was prepared in an analogous fashion to that described in Stage 13.1 using 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (Stage 25.2) and 4-fluoro-5-(tributylstannyl)-1H-pyrazole to afford an off-white powder. HPLC (Condition 4) tR=5.69 min, UPLC-MS (Condition 3) tR=1.09 min, m/z=415 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm.

Workup

  1. customto afford an off-white powder

Sources & evidence

ORD record
ord-daadfea8970f45eabd880d8089854eb8
Source dataset
uspto-grants-2014_09
Patent number
US08829195B2

Reaction notes

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