1H-pyrrolo(2,3-b)pyridin-5-amine → N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 1804742Notes

Reaction equation

HRID 1804742 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]2[CH:11]=[C:10]([C:12]([O:14]CC)=O)[N:9]([CH2:17][C:18]3[S:19][CH:20]=[CH:21][N:22]=3)[C:6]2=[N:7][CH:8]=1.[NH:25]1[C:29]2=[N:30][CH:31]=[C:32]([NH2:34])[CH:33]=[C:28]2[CH:27]=[CH:26]1.C[Al](C)C>>[NH:25]1[C:29]2=[N:30][CH:31]=[C:32]([NH:34][C:12]([C:10]3[N:9]([CH2:17][C:18]4[S:19][CH:20]=[CH:21][N:22]=4)[C:6]4=[N:7][CH:8]=[C:3]([C:2]([F:24])([F:23])[F:1])[CH:4]=[C:5]4[CH:11]=3)=[O:14])[CH:33]=[C:28]2[CH:27]=[CH:26]1

Participants

4

Reactant 3

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 16682925TrimethylaluminumHCID 66845785Ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate

Product 1

HCID 66846030N-(1H-Pyrrolo[2,3-b]pyrid-5-yl)-5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 62.2%

Procedure

Compound 30 was prepared according to a process similar to that described in step 5.1 by reacting 186 mg (0.523 mmol) of ethyl 5-trifluoromethyl-1-[(thiazol-2-yl)methyl]-1H-pyrrolo[2,3-b]pyridine-2-carboxylate prepared according to the protocol described in step 7.1 with 84 mg (0.628 mmol) of pyrrolo[2,3-b]pyrid-5-ylamine in the presence of 0.39 mL (0.785 mmol) of a solution of trimethylaluminium (2M/toluene). The product is collected by filtration, to give 144 mg of expected product.

Workup

  1. customCompound 30 was prepared
  2. customprepared
  3. filtrationThe product is collected by filtration

Sources & evidence

ORD record
ord-10242e7286ff4caabdf869921be525e1
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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