Dimethylformamide → HCID 58986361, compound

HRID 420798Notes

Reaction equation

HRID 420798 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([OH:17])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(C(C)C)CC)(C)C.[CH3:35][O:36][CH2:37]Cl.CN([CH:42]=[O:43])C>>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([O:17][CH2:35][O:36][CH3:37])=[CH:14][CH:15]=2)[C:10]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[C:9]1[CH:23]([CH3:24])[CH3:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1.[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:35]([O:36][CH2:37][O:43][CH3:42])=[CH:14][CH:15]=2)[C:10]([C:18]([OH:20])=[O:19])=[C:9]1[CH:23]([CH3:25])[CH3:24])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7864Chloromethyl Methyl EtherHCID 81531DiisopropylethylamineHCID 58986350HCID 58986350, compound2×

Product 2

HCID 58986361HCID 58986361, compoundHCID 66658644HCID 66658644, compound

Procedure

To a solution of 1-benzyl-5-hydroxy-2-isopropyl-1H-indole-3-carboxylic acid, ethyl ester (Compound 1, 345 mg, 1.0 mmol) in DMF (2 ml) was added diisopropylethylamine (iPr2NEt, 1.7 ml, 10.0 mmol) and chloromethyl methyl ether (MOMCl, 0.38 ml, 5.0 mmol). The mixture was stirred at room temperature for 72 h, and concentrated under vacuum, and purified by flash chromatography on silica gel eluting with 10-20% EtOAc-hexanes to yield 1-benzyl-2-isopropyl-5-(methoxymethoxy)-1H-indole-3-carboxylic acid, ethyl ester (Compound 2) as a clear oil.

Workup

  1. concentrationconcentrated under vacuum
  2. custompurified by flash chromatography on silica gel eluting with 10-20% EtOAc-hexanes

Sources & evidence

ORD record
ord-14e8c1ed478a41fcb6eea8d9592c9b62
Source dataset
uspto-grants-2012_01
Patent number
US08097644B2

Reaction notes

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