Acetic Acid → 2,5-Di-pyridin-3-yl-pyrrol-1-ylamine

HRID 1265294Notes

Reaction equation

HRID 1265294 reaction equation
C[Si](C)(C)CCOC(=O)[NH:7][N:8]1[C:12]([C:13]2[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=2)=[CH:11][CH:10]=[C:9]1[C:19]1[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(O)(=O)C>C1(C)C=CC=CC=1>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:12]2[N:8]([NH2:7])[C:9]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][CH:24]=3)=[CH:10][CH:11]=2)[CH:14]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8028TetrahydrofuranHCID 2724141Tetrabutylammonium FluorideHCID 69946665(2,5-Di-pyridin-3-yl-pyrrol-1-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester

Product 1

HCID 186154692,5-Di-pyridin-3-yl-pyrrol-1-ylamine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

(2,5-di-pyridin-3-yl-pyrrol-1-yl)-carbamic acid 2-trimethylsilanyl-ethyl ester (1 g, 2.6 mmol) is treated with a 1M solution of TBAF in THF (5.2 ml, 5.2 mmol). The resulting solution is stirred overnight under Ar at rt, then quenched with glacial acetic acid (0.3 ml, 5.2 mmol) and diluted with toluene. The resulting solution is passed through a short plug of silica gel and concentrated in vacuo to afford 2,5-Di-pyridin-3-yl-pyrrol-1-ylamine.

Workup

  1. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-860bc28069ef455db48f07619e7c5e7c
Source dataset
uspto-grants-2003_04
Patent number
US06545108B1

Reaction notes

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