Sodium Hydroxide → HCID 68696711, compound

HRID 2235175Notes

Reaction equation

HRID 2235175 reaction equation
[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][NH:22]3)=[CH:18][CH:17]=2)=[O:15])=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].[CH3:28][O:29][C:30]1[CH:35]=[CH:34][C:33]([CH3:36])=[CH:32][C:31]=1[S:37](Cl)(=[O:39])=[O:38]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6](=[O:25])[C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:14]([C:16]2[CH:24]=[C:23]3[C:19]([CH:20]=[CH:21][N:22]3[S:37]([C:31]3[CH:32]=[C:33]([CH3:36])[CH:34]=[CH:35][C:30]=3[O:29][CH3:28])(=[O:39])=[O:38])=[CH:18][CH:17]=2)=[O:15])=[CH:11][CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1451496-Methoxy-m-toluenesulfonyl chlorideHCID 68698623HCID 68698623, compound

Product 1

HCID 68696711HCID 68696711, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 94433Tetrabutylammonium hydrogen sulfateCatalyst

Procedure

A suspension of 4-[(1H-indole-6-carbonyl)-amino]-benzoic acid tert-butyl ester (200 mg, 0.595 mmol) and tetrabutylammonium hydrogensulfate (20 mg, 0.059 mmol) was treated with 50% aq. sodium hydroxide solution (0.30 mL, 7.4 mmol), then after 5 min 2-methoxy-5-methylbenzenesulfonyl chloride (0.197 mg, 0.892 mmol) was added, and the two-phase mixture was stirred for 1 h at room temperature. The reaction mixture was partitioned between water and ethyl acetate, the organic layer was washed with brine, dried (MgSO4), and evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) produced 4-{[1-(2-methoxy-5-methyl-benzenesulfonyl)-1H-indole-6-carbonyl]-amino}-benzoic acid tert-butyl ester (309 mg, 100%). Off-white solid, MS (ISP): m/e 521.3 (M+H).

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. washthe organic layer was washed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1bb70e5d8e1940bd9a1da353fc712425
Source dataset
uspto-grants-2010_05
Patent number
US07713996B2

Reaction notes

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