Hydrochloric Acid → [2-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) phenyl]methanol

HRID 1684004Notes

Reaction equation

HRID 1684004 reaction equation
[Br:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[C:20](O)=[O:21])=[C:8]2[CH3:27])=[CH:4][CH:3]=1.S(C)C.Cl.C(OCC)(=O)C>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]2[C:15]3[C:10](=[CH:11][C:12]([O:16][CH3:17])=[CH:13][CH:14]=3)[C:9]([C:18]3[CH:26]=[CH:25][CH:24]=[CH:23][C:19]=3[CH2:20][OH:21])=[C:8]2[CH3:27])=[CH:28][CH:29]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1068Dimethyl SulfideHCID 8857Ethyl AcetateHCID 538358182-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1 H-indol-3-yl) benzoic acid

Product 1

HCID 53681185[2-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1H-indol-3-yl) phenyl]methanolYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the acid from Step 1 (300 mg, 0.66 mmol) and BH3 Σ SMe2 (0.1 mL, 1 mmol) in THF (3 mL) was gently refluxed for 2 h. The cooled mixture was poured over icy dilute HCl and ethyl acetate. The organic layer was washed with brine and dried with MgSO4. Removal of the solvents yielded essentially pure product (285 mg).

Workup

  1. washThe organic layer was washed with brine
  2. dry with materialdried with MgSO4
  3. customRemoval of the solvents

Sources & evidence

ORD record
ord-25e6c5aab31546c49772fa68aa7db7e3
Source dataset
uspto-grants-1997_06
Patent number
US05639780

Reaction notes

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