Sodium hydride → HCID 19085314, compound

HRID 963092Notes

Reaction equation

HRID 963092 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC1C=CC=CC=1)=[O:11].[H-].[Na+].Br[CH:23]([CH3:32])[CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].ClC1C=CC=CC=1C(C1C=C(CC)SC=1N1C(C)=NN=C1CNC(C1N(CCCCCC(OCC)=O)C2C(C=1)=CC=CC=2)=O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.NCC1N(C2SC(CC)=CC=2C(=O)C2C=CC=CC=2Cl)C(C)=NN=1.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F>C(N(CC)CC)C.CN(C=O)C>[CH2:30]([O:29][C:27]([CH2:26][CH2:25][CH2:24][CH2:23][CH2:32][N:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([OH:12])=[O:11])=[O:28])[CH3:31]

Participants

9

Reactant 6

HCID 24758Sodium hydrideHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 7723355benzyl 1H-indole-2-carboxylateHCID 11499554HCID 11499554, compoundHCID 190850953-Aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole ditosylateHCID 67664386HCID 67664386, compound

Product 1

HCID 19085314HCID 19085314, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Procedure

1-(5-Ethoxycarbonylpentyl)indole-2-carboxylic acid was prepared using benzyl indole-2-carboxylate, DMF, sodium hydride (60% in oil) and ethyl 5-bromohexanoate, and ethyl 6-(2-((4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazol-3-yl)methylcarbamoyl)indol-1-yl)hexanoate was synthesized in the same manner as in Example 186 using 3-aminomethyl-4-(3-(2-chlorobenzoyl)-5-ethylthiophen-2-yl)-5-methyl[1,2,4]triazole di-p-toluenesulfonate, triethylamine and Bop reagent.

Sources & evidence

ORD record
ord-936009de2d194ea494b3c00867d77ec6
Source dataset
uspto-grants-1998_06
Patent number
US05760032

Reaction notes

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