Sodium hydride → HCID 10833640, compound

HRID 1069635Notes

Reaction equation

HRID 1069635 reaction equation
[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:25][C:26]([NH2:28])=[O:27])=[C:9]([CH2:23][CH3:24])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18](Cl)[CH:17]=1.ClC1C=C(CN2C3C(=C(O)C=CC=3)C(CC(N)=O)=C2CC)C=CC=1.[H-].[Na+].BrCC(OC)=O>CN(C=O)C>[CH3:1][O:2][C:3](=[O:29])[CH2:4][O:5][C:6]1[CH:14]=[CH:13][CH:12]=[C:11]2[C:7]=1[C:8]([CH2:25][C:26]([NH2:28])=[O:27])=[C:9]([CH2:23][CH3:24])[N:10]2[CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 10831199HCID 10831199, compoundHCID 10835627HCID 10835627, compound

Product 1

HCID 10833640HCID 10833640, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[[3-(2-Amino-2-oxoethyl)-1-[(3-chlorophenyl)methyl]-2-ethyl-1H-indol-4-yl]oxy]acetic acid methyl ester. (1-[(3-Chlorophenyl)methyl]-2-ethyl-4-hydroxy-1H-indole-3-acetamide (91 mg, 0.3 mmol) was reacted with 12 mg (0.3 mmol) of NaH/mineral oil (washed with hexanes) in 10 mL of DMF and then 0.03 mL (0.3 mmol) of methyl 2-bromoacetate as described in Example 75, Part H, to give after chromatography on silica gel (eluted with ethyl acetate) 80 mg (71% yield) of 2-[[3-(2-amino-2-oxoethyl)-2-ethyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]acetic acid methyl ester.

Sources & evidence

ORD record
ord-fe91d6b175a7481bb5401d18ac8314ad
Source dataset
uspto-grants-2001_06
Patent number
US06252084B1

Reaction notes

Loading…