Sodium hydride → 1-[(6-Chloro-5-methylpyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 1012415

Reaction equation

HRID 1012415 reaction equation
[C:1]1([C:7]2[NH:11][CH:10]=[C:9]([CH:12]=[O:13])[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[Cl:31][C:32]1[N:37]=[CH:36][C:35]([S:38](Cl)(=[O:40])=[O:39])=[CH:34][C:33]=1[CH3:42]>>[Cl:31][C:32]1[N:37]=[CH:36][C:35]([S:38]([N:11]2[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:8][C:9]([CH:12]=[O:13])=[CH:10]2)(=[O:40])=[O:39])=[CH:34][C:33]=1[CH3:42]

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 3633615-Crown-5HCID 110520905-Phenyl-1H-pyrrole-3-carboxaldehydeHCID 545941746-Chloro-5-methylpyridine-3-sulfonyl chloride

Product 1

HCID 866207591-[(6-Chloro-5-methylpyridin-3-yl)sulfonyl]-5-phenyl-1H-pyrrole-3-carbaldehyde

Procedure

By a reaction under similar conditions as in Reference Example 55 and using 5-phenyl-1H-pyrrole-3-carbaldehyde (171 mg), sodium hydride (60% in oil, 60 mg), 15-crown-5 (0.30 mL) and 6-chloro-5-methylpyridine-3-sulfonyl chloride (270 mg), the title compound was obtained as a solid (yield 244 mg, 68%).

Workup

  1. customBy a reaction under similar conditions as in Reference Example 55

Sources & evidence

ORD record
ord-c5f89f3c1edc494bafc8c61f431f15a1
Source dataset
uspto-grants-2011_07
Patent number
US07977488B2

Linked notes

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