2-Chlorobenzoxazole → HCID 22676839, compound

HRID 1006266Notes

Reaction equation

HRID 1006266 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:34]=[CH:35][CH:36]=1)[CH2:6][N:7]1[C:15]2[C:10](=[CH:11][C:12]([O:16][CH2:17][CH2:18][NH:19][CH3:20])=[CH:13][CH:14]=2)[C:9]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=2)=[C:8]1[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(N(C(C)C)CC)(C)C.Cl[C:47]1[O:48][C:49]2[CH:55]=[CH:54][CH:53]=[CH:52][C:50]=2[N:51]=1>CN(C)C=O.C(=O)(O)[O-].[Na+]>[O:48]1[C:49]2[CH:55]=[CH:54][CH:53]=[CH:52][C:50]=2[N:51]=[C:47]1[N:19]([CH3:20])[CH2:18][CH2:17][O:16][C:12]1[CH:11]=[C:10]2[C:15](=[CH:14][CH:13]=1)[N:7]([CH2:6][C:5]1[CH:34]=[CH:35][CH:36]=[C:3]([O:2][CH3:1])[CH:4]=1)[C:8]([C:29]([O:31][CH2:32][CH3:33])=[O:30])=[C:9]2[C:21]1[CH:22]=[CH:23][C:24]([O:27][CH3:28])=[CH:25][CH:26]=1

Participants

6

Reactant 3

HCID 119862-ChlorobenzoxazoleHCID 81531DiisopropylethylamineHCID 22676742HCID 22676742, compound

Product 1

HCID 22676839HCID 22676839, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of Ethyl 1-(3-methoxybenzyl)-3-(4-methoxyphenyl)-5-[2-(methylamino)ethoxy]-1H-indole-2-carboxylate (Example 156, 100 mg, 0.2028 mmol) in N,N-dimethylformamide (1.5 ml) was added diisopropylethylamine (0.09 ml, 0.5167 mmol, 2.5 eq.) and 2-chlorobenzoxazole (0.03 ml, 0.2636 mmol, 1.3 eq.). The reaction mixture was heated at 120° C. for 4 hr. After cooling the reaction was diluted with saturated aqueous sodium bicarbonate and then extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo and purified by flash column (silica gel, dichloromethane to dichloromethane:methanol 95:5). The desired product was obtained as a light yellow oil in 97% yield (119 mg), MS (M+H)=606.3, Rf=0.69 (dichloromethane/methanol 95:5).

Workup

  1. temperatureAfter cooling the reaction
  2. extractionextracted with ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo
  6. custompurified by flash column (silica gel, dichloromethane to dichloromethane:methanol 95:5)

Sources & evidence

ORD record
ord-ac418d80c7e14fc2bb1346103850165e
Source dataset
uspto-grants-2004_09
Patent number
US06787651B2

Reaction notes

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