Potassium Carbonate → 6-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-indole-1-carboxylic acid tert-butyl ester

HRID 746457Notes

Reaction equation

HRID 746457 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH2:17])[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:18][C:19]1[N:20]=[C:21](Br)[C:22]2[N:23]([CH:25]=[CH:26][N:27]=2)[CH:24]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:21]3[C:22]4[N:23]([CH:25]=[CH:26][N:27]=4)[CH:24]=[C:19]([Br:18])[N:20]=3)[CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 150258436,8-Dibromoimidazo[1,2-a]pyrazineHCID 22240525tert-Butyl 6-amino-1H-indole-1-carboxylate

Product 1

HCID 865979236-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-indole-1-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A quantity of 0.23 g (1 mmole) of 6-Amino-indole-1-carboxylic acid tert-butyl ester is treated with 0.27 g (1 mmole) of 6,8-Dibromo-imidazo[1,2-a]pyrazine in acetonitrile with 3 eq. of K2CO3 at reflux for 16 hrs. The reaction mixture is cooled partitioned between ethyl acetate and water, the organic extracts are dried over anhydrous MgSO4 and evaporated in vacuo to afford 6-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-indole-1-carboxylic acid tert-butyl ester. 6-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-indole-1-carboxylic acid tert-butyl ester is treated with an excess of TFA in dichloromethane at room temperature for 2 hrs. The reaction solution is evaporated in vacuo and partitioned between saturated Na2CO3 and ethyl acetate; the organic extracts are dried over anhydrous MgSO4 and evaporated in vacuo to afford (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indol-6-yl)-amine.

Workup

  1. temperatureat reflux for 16 hrs
  2. temperatureThe reaction mixture is cooled
  3. custompartitioned between ethyl acetate and water
  4. dry with materialthe organic extracts are dried over anhydrous MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-a2e838b5f8804d81949dc163f502225f
Source dataset
uspto-grants-2008_07
Patent number
US07393848B2

Reaction notes

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