Dichloromethane → HCID 56599017, compound

HRID 2283618Notes

Reaction equation

CB1OB(C)OB(C)O1.ClCCl.[C:13](=O)([O-])[O-].[K+].[K+].COC1C=C(OC)C=CC=1C[N:24]([C:52]1[S:56][N:55]=[CH:54][N:53]=1)[S:25]([C:28]1[CH:33]=[CH:32][C:31]([O:34][C:35]2[CH:40]=[CH:39][C:38]([C:41]([F:44])([F:43])[F:42])=[CH:37][C:36]=2[C:45]2[CH:50]=[CH:49][N:48]=[N:47][CH:46]=2)=[C:30](I)[CH:29]=1)(=[O:27])=[O:26].CC1CCCO1>>[CH3:13][C:30]1[CH:29]=[C:28]([S:25]([NH:24][C:52]2[S:56][N:55]=[CH:54][N:53]=2)(=[O:27])=[O:26])[CH:33]=[CH:32][C:31]=1[O:34][C:35]1[CH:40]=[CH:39][C:38]([C:41]([F:43])([F:42])[F:44])=[CH:37][C:36]=1[C:45]1[CH:50]=[CH:49][N:48]=[N:47][CH:46]=1

Participants

Reactant 5

HCID 6344Dichloromethane

HCID 73012-Methyltetrahydrofuran

HCID 11430Potassium Carbonate

HCID 574072Trimethylboroxine

HCID 66652980N-(2,4-dimethoxybenzyl)-3-iodo-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 56599017HCID 56599017, compound

Conditions

Temperature: 80 °C

Procedure

A Reactivial™ containing trimethylboroxine (798 mg, 6.36 mmol), 1,1-bis(diphenylphosphino)ferrocenepalladium(II)dichloride, complex with dichloromethane (26 mg, 0.03 mmol), potassium carbonate (88 mg, 0.64 mmol), N-(2,4-dimethoxybenzyl)-3-iodo-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide (Preparation 38, 240 mg, 0.32 mmol) and 2-methyltetrahydrofuran (5 mL) was sparged with nitrogen and heated to 80° C. for 24 hours. The reaction mixture was cooled and purified directly by silica gel column chromatography (0% to 20% methanol in ethyl acetate gradient elution) followed by reverse phase HPLC to afford the title compound.

Workup

customwas sparged with nitrogen
temperatureThe reaction mixture was cooled
custompurified directly by silica gel column chromatography (0% to 20% methanol in ethyl acetate gradient elution)

Sources & evidence

ORD record: ord-fcc06bce23904dfc94f58bbe02504460
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09145407B2

Reaction notes

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