HCID 57942589, compound → HCID 58268249, compound

HRID 1898290Notes

Reaction equation

HRID 1898290 reaction equation
Br[C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[C:4]([CH3:27])[N:3]=1.C([Mg]Cl)(C)C.[C:33]([Si:37]([CH3:50])([CH3:49])[N:38]1[C:42]2[N:43]=[CH:44][CH:45]=[C:46]([CH:47]=[O:48])[C:41]=2[CH:40]=[CH:39]1)([CH3:36])([CH3:35])[CH3:34]>C1COCC1>[C:33]([Si:37]([CH3:50])([CH3:49])[N:38]1[C:42]2=[N:43][CH:44]=[CH:45][C:46]([CH:47]([OH:48])[C:2]3[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]4[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=4)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[C:4]([CH3:27])[N:3]=3)=[C:41]2[CH:40]=[CH:39]1)([CH3:36])([CH3:35])[CH3:34]

Participants

5

Reactant 3

HCID 57942589HCID 57942589, compoundHCID 58268032HCID 58268032, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 58268249HCID 58268249, compoundYield 145%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-(2-Bromo-5-chloro-6-methyl-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (152.7 mg, 0.3 mmol) in 2 ml of THF under nitrogen atmosphere at 0° C. was added via syringe 2.0M isopropyl magnesium chloride (0.36 ml, 0.72 mmol). The reaction mixture was stirred for about 45 minutes and 1-(tert-Butyl-dimethyl-silanyl)-1H-pyrrolo[2,3-b]pyridine-4-carbaldehyde (54 mg, 0.21 mmol) was added and the resultant mixture was stirred for 30 minutes at 0° C. and then 2 hours at room temperature. The mixture was quenched with saturated ammonium chloride and extracted with ethyl acetate. The organic layer was separated and washed with water twice and dried. Concentration of this mixture afforded the crude product (210 mg) which was used in the next step without any further purification. MS (ES) (M++H) expect 689. found 688.9

Workup

  1. custom2 hours
  2. customat room temperature
  3. customThe mixture was quenched with saturated ammonium chloride
  4. extractionextracted with ethyl acetate
  5. customThe organic layer was separated
  6. washwashed with water twice
  7. customdried

Sources & evidence

ORD record
ord-a2f24d868d604e9d80c67f3fb0d1bfa6
Source dataset
uspto-grants-2013_08
Patent number
US08519135B2

Reaction notes

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