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Dichloromethane → HCID 56599017, compound

HRID 2283618
Notes
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Reaction equation

HRID 2283618 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 5

HCID 6344DichloromethaneHCID 73012-MethyltetrahydrofuranHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 66652980N-(2,4-dimethoxybenzyl)-3-iodo-4-[2-pyridazin-4-yl-4-(trifluoromethyl)phenoxy]-N-1,2,4-thiadiazol-5-ylbenzenesulfonamide

Product 1

HCID 56599017
HCID 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

  1. customwas sparged with nitrogen
  2. temperatureThe reaction mixture was cooled
  3. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes