1H-pyrrolo(2,3-b)pyridin-5-amine → HCID 66846526, compound

HRID 1804740Notes

Reaction equation

HRID 1804740 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=1)[C:6]([C:19](OC)=[O:20])=[CH:5]2.[NH:23]1[C:27]2=[N:28][CH:29]=[C:30]([NH2:32])[CH:31]=[C:26]2[CH:25]=[CH:24]1.C[Al](C)C>>[NH:23]1[C:27]2=[N:28][CH:29]=[C:30]([NH:32][C:19]([C:6]3[N:7]([CH2:11][C:12]4[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[CH:13]=4)[C:8]4[C:9]([CH:5]=3)=[CH:10][C:2]([F:1])=[CH:3][CH:4]=4)=[O:20])[CH:31]=[C:26]2[CH:25]=[CH:24]1

Participants

4

Reactant 3

HCID 117151871H-pyrrolo(2,3-b)pyridin-5-amineHCID 16682925TrimethylaluminumHCID 66845713HCID 66845713, compound

Product 1

HCID 66846526HCID 66846526, compoundYield 39.9%

Procedure

Compound 5 was prepared according to a process similar to that described in step 5.2 by reacting 200 mg (0.673 mmol) of methyl 5-fluoro-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxylate prepared according to the protocol described in step 6.1 with 107 mg (0.807 mmol) of pyrrolo[2,3-b]pyrid-5-ylamine in the presence of 0.5 mL (1.01 mmol) of a solution of trimethylaluminium (2M/toluene). The product is collected by filtration, to give 107 mg of the expected product.

Workup

  1. customCompound 5 was prepared
  2. customprepared
  3. filtrationThe product is collected by filtration

Sources & evidence

ORD record
ord-50b3cc4bf2014af28fba222a7e119070
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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