Sodium hydride → HCID 19769834, compound

HRID 1723286Notes

Reaction equation

[CH3:1][C:2]1[N:6]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:5]=[N:4][C:3]=1[CH2:26][CH:27]1[C:39](=[O:40])[C:38]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[NH:31][C:30]=2[CH2:29][CH2:28]1.[H-].[Na+].C1(C)C=CC(S(O[CH2:53][CH:54]2[CH2:58][CH2:57][CH2:56][CH2:55]2)(=O)=O)=CC=1>>[CH:54]1([CH2:53][N:31]2[C:30]3[CH2:29][CH2:28][CH:27]([CH2:26][C:3]4[N:4]=[CH:5][N:6]([C:7]([C:8]5[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=5)([C:14]5[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=5)[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)[C:2]=4[CH3:1])[C:39](=[O:40])[C:38]=3[C:37]3[C:32]2=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:58][CH2:57][CH2:56][CH2:55]1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 12568544Cyclopentylmethyl 4-methylbenzene-1-sulfonate

HCID 19769831HCID 19769831, compound

Product 1

HCID 19769834HCID 19769834, compoundYield 48.9%

Procedure

Using the procedures described above for Intermediate 10, 1,2,3,9-tetrahydro-3-[[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]methyl]-4H-carbazol-4-one (500 mg) was treated with sodium hydride (73% dispersion in oil; 38 mg) and was then stirred with cyclopentanemethanol (p-toluenesulphonate) (292 mg) for 24 h. Work up and FCC was described above gave the title compound (283 mg), p.p. 177°-179°.

Sources & evidence

ORD record: ord-af1a962c39e14f0ea98b36e366cbdcfd
Source dataset: uspto-grants-1989_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04859662

Reaction notes

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