1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]benzoate

HRID 2177803Notes

Reaction equation

HRID 2177803 reaction equation
C1(S(CC2C(C(OCC)=O)=C(O)C(C3C=COC=3)=CC=2)(=O)=O)C=CC=CC=1.[C:28]1([S:34]([CH2:37][C:38]2[C:43]([C:44]([O:46][CH3:47])=[O:45])=[C:42](OS(C(F)(F)F)(=O)=O)[C:41]([CH2:56][CH3:57])=[CH:40][CH:39]=2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[O:58]1[CH2:63][CH2:62][CH2:61][CH2:60][CH:59]1[N:64]1[C:68](B2OC(C)(C)C(C)(C)O2)=[CH:67][CH:66]=[N:65]1>>[C:28]1([S:34]([CH2:37][C:38]2[C:43]([C:44]([O:46][CH3:47])=[O:45])=[C:42]([C:68]3[N:64]([CH:59]4[CH2:60][CH2:61][CH2:62][CH2:63][O:58]4)[N:65]=[CH:66][CH:67]=3)[C:41]([CH2:56][CH3:57])=[CH:40][CH:39]=2)(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 3

HCID 115872081-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67107629Ethyl 6-benzenesulphonylmethyl-3-(furan-3-yl)-2-hydroxybenzoateHCID 86677116Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-(trifluoromethanesulphonyloxy)benzoate2×

Product 1

HCID 67107802Methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-[2-(tetrahydropyran-2-yl)-2H-pyrazol-3-yl]benzoate

Procedure

Prepared by proceeding in a similar manner to Intermediate 36, starting from methyl 6-(benzenesulphonylmethyl)-3-ethyl-2-(trifluoromethanesulphonyloxy)benzoate (Intermediate 127) and 1-(2-tetrahydropyranyl)-1H-pyrazole-5-boronic acid pinacol ester as an opaque foam which was used without further characterization.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-cc5daac8481843909d9a9c587955de90
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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