Sodium hydride → HCID 66802256, compound

HRID 589770Notes

Reaction equation

HRID 589770 reaction equation
[N:1]1([CH2:6][CH2:7][OH:8])[CH:5]=[CH:4][CH:3]=[CH:2]1.[H-].[Na+].[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[S:19][C:18]([S:20]([NH:23][C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27](OC)=[O:28])(=[O:22])=[O:21])=[C:17]([CH3:34])[C:16]=2[CH:35]=1>C1COCC1>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]2[S:19][C:18]([S:20]([NH:23][C:24]3[CH:25]=[C:26]([CH:31]=[CH:32][CH:33]=3)[C:27]([O:8][CH2:7][CH2:6][N:1]3[CH:5]=[CH:4][CH:3]=[CH:2]3)=[O:28])(=[O:22])=[O:21])=[C:17]([CH3:34])[C:16]=2[CH:35]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 109754381-(2-Hydroxyethyl)pyrroleHCID 56941887HCID 56941887, compound

Product 1

HCID 66802256HCID 66802256, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of 2-pyrrol-1-yl-ethanol (17 mg, 0.15 mmol) and NaH (5 mg, 60% dispersion in mineral oil, 0.13 mmol) in THF (200 μL) was stirred at 0° C. for 15 min. A solution of methyl 3-{[(5-chloro-3-methyl-1-benzothien-2-yl)sulfonyl]amino}benzoate (Example 74) (20 mg, 0.05 mmol) in THF (100 μL) was added, and the reaction mixture was stirred at 0° C. for another 6 h. The reaction was quenched by addition of cold MeOH and 4:1 water/HOAc (50 μL) before purified by preparative HPLC. The title compound was obtained in 53% yield (12.5 mg). MS (ESI+) m/z 475 [M+H]+.

Workup

  1. stirringthe reaction mixture was stirred at 0° C. for another 6 h
  2. customThe reaction was quenched by addition of cold MeOH and 4:1 water/HOAc (50 μL)
  3. custombefore purified by preparative HPLC

Sources & evidence

ORD record
ord-2dd04b8e3fa54703afec9d7644faa876
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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