Triethylamine → HCID 59729574, compound

HRID 403326Notes

Reaction equation

HRID 403326 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([CH:26]([CH3:28])[CH3:27])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[CH3:35][N:36]1[C:44]2[C:39](=[CH:40][C:41]([NH2:45])=[CH:42][CH:43]=2)[C:38](C)=[CH:37]1.C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:17]=[C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:15]([CH:26]([CH3:28])[CH3:27])=[CH:14][C:10]=1[C:11]([NH:45][C:41]1[CH:40]=[C:39]2[C:44](=[CH:43][CH:42]=1)[N:36]([CH3:35])[CH:37]=[CH:38]2)=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 591678792,4-Dibenzyloxy-5-isopropyl-benzoic acidHCID 595509931,3-Dimethyl-1H-indol-5-amine

Product 1

HCID 59729574HCID 59729574, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

2,4-Dibenzyloxy-5-isopropylbenzoic acid (5.64 g, 15.0 mmol, 1.00 equiv.) in 80 mL dichloromethane at room temperature was treated with oxalyl chloride (2.00 g, 15.75 mmol, 1.05 equiv.) and catalytic amount of DMF (0.1 mL) for 1 hour. Solvent and excess (COCl)2 were removed on rotary evaporator. The residue was dissolved in 100 mL dichloromethane, and treated with 1,3-dimethyl-5-aminoindole (2.40 g, 15.0 mmol, 1.00 equiv.) and triethylamine (2.28 g, 22.5 mmol, 1.50 equiv.) at 0° C. for one hour. Normal aqueous workup and removal of solvent gave a light brown solid that was washed with ether to yield 2,4-dibenzyloxy-5-isopropyl-N-(1-methyl-1H-indol-5-yl)-benzamide (A) as off-white solid (7.20 g, 14.3 mmol, 95%)

Workup

  1. customSolvent and excess (COCl)2 were removed on rotary evaporator
  2. dissolutionThe residue was dissolved in 100 mL dichloromethane
  3. customNormal aqueous workup and removal of solvent
  4. customgave a light brown solid that
  5. washwas washed with ether

Sources & evidence

ORD record
ord-3e48fbccac514504bf49d4e5e4bd0b09
Source dataset
uspto-grants-2014_06
Patent number
US08748424B2

Reaction notes

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