Sodium hydride → 1-(2,3-Dihydro-1,4-benzodioxin-5-ylsulfonyl)-4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

HRID 554334Notes

Reaction equation

[CH3:1][C:2]1[C:3]([CH:13]=[O:14])=[CH:4][NH:5][C:6]=1[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[H-].[Na+].C1OCCOCCOCCOCCOC1.[O:32]1[C:37]2[CH:38]=[CH:39][CH:40]=[C:41]([S:42](Cl)(=[O:44])=[O:43])[C:36]=2[O:35][CH2:34][CH2:33]1>>[O:32]1[C:37]2[CH:38]=[CH:39][CH:40]=[C:41]([S:42]([N:5]3[C:6]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[C:2]([CH3:1])[C:3]([CH:13]=[O:14])=[CH:4]3)(=[O:44])=[O:43])[C:36]=2[O:35][CH2:34][CH2:33]1

Participants

Reactant 4

HCID 24758Sodium hydride

HCID 3633615-Crown-5

HCID 470029742,3-Dihydro-1,4-benzodioxine-5-sulfonyl chloride

HCID 713628124-Methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

Product 1

HCID 866207621-(2,3-Dihydro-1,4-benzodioxin-5-ylsulfonyl)-4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde

Procedure

Using 4-methyl-5-phenyl-1H-pyrrole-3-carbaldehyde (185 mg), sodium hydride (60% in oil, 116 mg), 15-crown-5 (881 mg) and 2,3-dihydro-1,4-benzodioxine-5-sulfonyl chloride (516 mg), a procedure as in Reference Example 219 was performed to give the title compound as a pale-yellow amorphous (yield 295 mg, 77%).

Sources & evidence

ORD record: ord-d4634a7ab51f4ffe89c8258dc618e515
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08048909B2

Reaction notes

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