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Sodium hydride → HCID 58042316, compound

HRID 1619689
Notes
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Reaction equation

HRID 1619689 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)[CH:5]=1.[C:17]([C:19]1[CH:20]=[C:21]([S:26]([N:29]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=2[O:44][CH3:45])[C:30]2[S:31][CH:32]=[CH:33][N:34]=2)(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1F)#[N:18]>CN(C=O)C.C(OCC)(=O)C>[Br:3][C:4]1[CH:9]=[CH:8][C:7]([O:10][C:24]2[CH:23]=[CH:22][C:21]([S:26]([N:29]([CH2:35][C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][C:37]=3[O:44][CH3:45])[C:30]3[S:31][CH:32]=[CH:33][N:34]=3)(=[O:28])=[O:27])=[CH:20][C:19]=2[C:17]#[N:18])=[C:6]([C:11]2[N:15]([CH3:16])[N:14]=[CH:13][CH:12]=2)[CH:5]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 58042307HCID 58042307, compoundHCID 136200892HCID 136200892, compound

Product 1

HCID 58042316HCID 58042316, compoundYield 87.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×
HCID 8857
Ethyl Acetate
Solvent

Procedure

To a slurry of sodium hydride (54 mg, 1.4 mmol, 60% in mineral oil) in DMF (1 mL) was added 4-bromo-2-(1-methyl-1H-pyrazol-5-yl)phenol (Preparation 89, 210 mg, 0.83 mmol) as a solution in DMF (3 mL). After stirring for 30 minutes, 3-cyano-N-(2,4-dimethoxy-benzyl)-4-fluoro-N-thiazol-2-yl-benzenesulfonamide (Preparation 90, 415 mg, 0.957 mmol) was added. After 3 hours the reaction mixture was diluted with ethyl acetate (10 mL) and washed with water (5 mL) and brine (5 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. Purification by automated flash column chromatography using a 0-100% ethyl acetate/dichloromethane gradient provided the title compound (482 mg, 87%) as a yellow foam.

Workup

  1. washwashed with water (5 mL) and brine (5 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by automated flash column chromatography

Sources & evidence

ORD record
ord-9ef65792672c49e4bb8a3d28c0d057d0
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772293B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes