5-(4-(4-(2-(benzyloxy)ethyl)piperazin-1-yl)phenyl)-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine → 2-(4-(4-(3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazin-1-yl)ethanol

HRID 531540Notes

Reaction equation

C([O:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([C:23]3[CH:24]=[C:25]4[C:31]([C:32]5[C:33]([CH3:46])=[N:34][N:35]([CH2:38][C:39]6[CH:44]=[CH:43][CH:42]=[C:41]([F:45])[CH:40]=6)[C:36]=5[CH3:37])=[CH:30][N:29]([S:47]([C:50]5[CH:56]=[CH:55][C:53]([CH3:54])=[CH:52][CH:51]=5)(=[O:49])=[O:48])[C:26]4=[N:27][CH:28]=3)=[CH:19][CH:18]=2)[CH2:13][CH2:12]1)C1C=CC=CC=1>FC(F)(F)C(O)=O.C1(C)C=CC=CC=1>[F:45][C:41]1[CH:40]=[C:39]([CH:44]=[CH:43][CH:42]=1)[CH2:38][N:35]1[C:36]([CH3:37])=[C:32]([C:31]2[C:25]3[C:26](=[N:27][CH:28]=[C:23]([C:20]4[CH:21]=[CH:22][C:17]([N:14]5[CH2:13][CH2:12][N:11]([CH2:10][CH2:9][OH:8])[CH2:16][CH2:15]5)=[CH:18][CH:19]=4)[CH:24]=3)[N:29]([S:47]([C:50]3[CH:51]=[CH:52][C:53]([CH3:54])=[CH:55][CH:56]=3)(=[O:48])=[O:49])[CH:30]=2)[C:33]([CH3:46])=[N:34]1

Participants

Conditions

Temperature: 70 °C

Procedure

5-(4-(4-(2-(benzyloxy)ethyl)piperazin-1-yl)phenyl)-3-(1-(3-fluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (150 mg, 0.195 mmol) was dissolved in trifluoroacetic acid/toluene (5/5 ml) and heated to 70° C. for overnight. Solvents evaporated off to yield 208 mg of the crude titled compound.

Workup

customSolvents evaporated off

Sources & evidence

ORD record: ord-5b4d98dc7c46473fa245c0ae7f9b27eb
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353107B2

Reaction notes

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