tert-Butyl 4-bromo-1H-indole-1-carboxylate → 4-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-indole-1-carboxylic Acid tert-Butyl Ester

HRID 751311Notes

Reaction equation

HRID 751311 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12](Br)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24]1[C:25](B(O)O)=[C:26]2[CH2:31][CH2:30][CH2:29][N:27]2[N:28]=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[C:12]([C:25]3[C:24]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][N:18]=4)=[N:28][N:27]4[CH2:29][CH2:30][CH2:31][C:26]=34)[CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 40425427tert-Butyl 4-bromo-1H-indole-1-carboxylateHCID 59710031(2-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid

Product 1

HCID 586119614-[2-(Pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-indole-1-carboxylic Acid tert-Butyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The titled intermediate was made via Preparation 33 (General Suzuki Coupling Method D) from 4-bromo-indole-1-carboxylic acid tert-butyl ester and 2-(pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 5). MS (ESI) m/e 401 (M+1). TLC (SiO2): Rf0.5 (1:1 methylene chloride/[80:18:2 chloroform/methanol/concentrated aqueous ammonium hydroxide]).

Sources & evidence

ORD record
ord-f560e80ea8f94713961b306c55110111
Source dataset
uspto-grants-2008_07
Patent number
US07405299B2

Reaction notes

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