Trifluoroacetic acid → (6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indol-6-yl)-amine

HRID 746458Notes

Reaction equation

HRID 746458 reaction equation
C(OC([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([NH:17][C:18]3[C:19]4[N:20]([CH:25]=[CH:26][N:27]=4)[CH:21]=[C:22]([Br:24])[N:23]=3)[CH:15]=2)[CH:10]=[CH:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>ClCCl>[Br:24][C:22]1[N:23]=[C:18]([NH:17][C:14]2[CH:15]=[C:16]3[C:11]([CH:10]=[CH:9][NH:8]3)=[CH:12][CH:13]=2)[C:19]2[N:20]([CH:25]=[CH:26][N:27]=2)[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865979236-(6-Bromo-imidazo[1,2-a]pyrazin-8-ylamino)-indole-1-carboxylic acid tert-butyl ester

Product 1

HCID 57447604(6-Bromo-imidazo[1,2-a]pyrazin-8-yl)-(1H-indol-6-yl)-amine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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. customThe reaction solution is evaporated in vacuo
  2. custompartitioned between saturated Na2CO3 and ethyl acetate
  3. dry with materialthe organic extracts are dried over anhydrous MgSO4
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-ae13e810eb384f03a142467fadc2bf22
Source dataset
uspto-grants-2008_07
Patent number
US07393848B2

Reaction notes

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