2-Bromoethyl methyl ether → 2-Tert-butoxy-2-[4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-7-oxo-pyrrolo[2,3-c]pyridin-5-yl]acetic acid

HRID 1473194Notes

Reaction equation

HRID 1473194 reaction equation
[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[NH:19][CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[CH3:29][O:30][CH2:31][CH2:32]Br>>[C:1]([O:5][CH:6]([C:11]1[N:16]([CH3:17])[C:15](=[O:18])[C:14]2[N:19]([CH2:32][CH2:31][O:30][CH3:29])[CH:20]=[CH:21][C:13]=2[C:12]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:7]([OH:9])=[O:8])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 809722-Bromoethyl methyl etherHCID 89463134methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate

Product 1

HCID 715345222-Tert-butoxy-2-[4-(4-chlorophenyl)-1-(2-methoxyethyl)-6-methyl-7-oxo-pyrrolo[2,3-c]pyridin-5-yl]acetic acid

Procedure

The title compound was prepared in a manner similar to that described in Example 2 from methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate and 2-bromoethyl methyl ether. 1H NMR (400 MHz, CHLOROFORM-d) ppm 7.59-7.65 (m, 1H) 7.45-7.51 (m, 2H) 7.39-7.45 (m, 1H) 7.10-7.16 (m, 1H) 5.91-5.99 (m, 1H) 5.30-5.38 (m, 1H) 4.67-4.87 (m, 2H) 3.72-3.86 (m, 2H) 3.67 (s, 3H)) 3.34 (s, 3H) 1.01 (s, 9H); LCMS (m/z) ES+=447 (M+1).

Sources & evidence

ORD record
ord-524c1a0c474c40b797b48588663a33fa
Source dataset
uspto-grants-2015_04
Patent number
US09012642B2

Reaction notes

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