3-chloro-1-(4-isopropoxyphenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester → HCID 68701140, compound

HRID 646159Notes

Reaction equation

HRID 646159 reaction equation
C([O:3][C:4]([C:6]1[N:7]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=2)[C:8]2[C:13]([C:14]=1[Cl:15])=[CH:12][C:11](B1OC(C)(C)C(C)(C)O1)=[CH:10][CH:9]=2)=[O:5])C.Br[C:36]1[N:41]=[CH:40][C:39]([NH:42][CH:43]2[CH2:47][CH2:46][CH2:45][CH2:44]2)=[CH:38][CH:37]=1>>[Cl:15][C:14]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([C:36]3[CH:37]=[CH:38][C:39]([NH:42][CH:43]4[CH2:47][CH2:46][CH2:45][CH2:44]4)=[CH:40][N:41]=3)[CH:12]=2)[N:7]([C:25]2[CH:30]=[CH:29][C:28]([O:31][CH:32]([CH3:34])[CH3:33])=[CH:27][CH:26]=2)[C:6]=1[C:4]([OH:3])=[O:5]

Participants

3

Reactant 2

HCID 687004313-chloro-1-(4-isopropoxyphenyl)-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl esterHCID 722192236-Bromo-N-cyclopentylpyridin-3-amine

Product 1

HCID 68701140HCID 68701140, compound

Procedure

The title compound was prepared in accordance with Example 8(b) from 3-chloro-1-(4-isopropoxyphenyl)-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-indole-2-carboxylic acid ethyl ester (see Example 35, Method 1, step (c)) and 6-bromopyrid-3-ylcyclopentylamine (see Example 45(b)), followed by ester hydrolysis according to Example 35, Method 3, step (b).

Sources & evidence

ORD record
ord-db4e370ae60d4c15830eab05a7d12c26
Source dataset
uspto-grants-2010_04
Patent number
US07705023B2

Reaction notes

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