p-Toluenesulfonic acid → 1-(1,1,1-Trifluoro-2-methylpropan-2-yl)-1H-pyrrolo[2,3-b]pyridine-3-carbonitrile

HRID 624658Notes

Reaction equation

[CH3:1][C:2]1C=CC(S(O)(=O)=O)=C[CH:3]=1.[NH2:12][C:13]1[N:17]([C:18]([CH3:24])([CH3:23])[C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:25]#[N:26])[CH:14]=1.COC(OC)CC(OC)OC>C1(C)C=CC=CC=1>[F:21][C:19]([F:22])([F:20])[C:18]([N:17]1[C:13]2=[N:12][CH:1]=[CH:2][CH:3]=[C:14]2[C:15]([C:25]#[N:26])=[CH:16]1)([CH3:23])[CH3:24]

Participants

Conditions

Temperature: 100 °C

Procedure

4-Methylbenzenesulfonic acid (10.57 mg, 0.061 mmol) was added in one portion to a solution of 5-amino-1-(1,1,1-trifluoro-2-methylpropan-2-yl)-1H-pyrrole-3-carbonitrile (133.3 mg, 0.614 mmol) and 1,1,3,3-tetramethoxypropane (111 μl, 0.675 mmol) in toluene (1227 μl) at RT. The mixture was heated at 100° C. for 1 h and purified directly by HPLC to afford the title compound as a brown solid.

Workup

custompurified directly by HPLC

Sources & evidence

ORD record: ord-e53606db2fba49fb9810438870203648
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303045B2

Reaction notes

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