HCID 22663271, compound → HCID 22663214, compound

HRID 392190Notes

Reaction equation

HRID 392190 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([Cl:32])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:30]=[O:31])=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:13][CH:12]=1)=[O:10].[CH3:33][Mg]Br>O1CCCC1.C(OCC)C>[Cl:32][C:6]1[CH:5]=[N:4][CH:3]=[C:2]([Cl:1])[C:7]=1[NH:8][C:9]([C:11]1[CH:19]=[C:18]2[C:14]([C:15]([CH:30]([OH:31])[CH3:33])=[CH:16][N:17]2[S:20]([C:23]2[CH:28]=[CH:27][C:26]([CH3:29])=[CH:25][CH:24]=2)(=[O:22])=[O:21])=[CH:13][CH:12]=1)=[O:10]

Participants

5

Reactant 2

HCID 22663271HCID 22663271, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22663214HCID 22663214, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

A stirred solution of N-(3,5-dichloro-pyridin-4-yl)-3-formyl-1-(toluene-4-sulphonyl)-1H-indole-6-carboxamide (0.1 g, Example 17) in tetrahydofuran (3 ml), at 0° C., was treated with a solution of methylmagnesium bromide in diethyl ether (0.11 ml, 3M). The mixture was allowed to warm to room temperature then stirred for 2 hours. The reaction mixture was quenched with water (15 ml) and then extracted with ethyl acetate (15 ml). The organic extract was dried over sodium sulphate then evaporated. The residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1, v/v) to yield the title compound (68 mg) as a white solid, m.p. 206-21 1° C. [Elemental analysis:— C, 55.07; H, 4.00; N, 7.92%. Calculated for C23H19Cl2N3O4S:— C, 54.77; H, 3.80; N, 8.33%].

Workup

  1. customThe reaction mixture was quenched with water (15 ml)
  2. extractionextracted with ethyl acetate (15 ml)
  3. extractionThe organic extract
  4. dry with materialwas dried over sodium sulphate
  5. customthen evaporated
  6. additionThe residue was subjected to flash column chromatography on silica eluting with a mixture of ethyl acetate and hexane (2:1

Sources & evidence

ORD record
ord-fd4d6076e6504b7299d1d00ef78f7035
Source dataset
uspto-grants-2004_10
Patent number
US06800645B1

Reaction notes

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