tert-butyl 4-((4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate → 5,6-difluoro-1-(phenylsulfonyl)-3-(1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl)-1H-indole

HRID 2274791Notes

Reaction equation

HRID 2274791 reaction equation
FC1C=C2C(C(C3C=NN(CC4CCNCC4)C=3)=CN2S(C2C=CC=CC=2)(=O)=O)=CC=1.[F:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][C:41]=1[F:42])[N:38]([S:43]([C:46]1[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1)(=[O:45])=[O:44])[CH:37]=[C:36]2[C:52]1[CH:53]=[N:54][N:55]([CH2:57][CH:58]2[CH2:63][CH2:62][N:61](C(OC(C)(C)C)=O)[CH2:60][CH2:59]2)[CH:56]=1>>[F:32][C:33]1[CH:34]=[C:35]2[C:39](=[CH:40][C:41]=1[F:42])[N:38]([S:43]([C:46]1[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=1)(=[O:44])=[O:45])[CH:37]=[C:36]2[C:52]1[CH:53]=[N:54][N:55]([CH2:57][CH:58]2[CH2:63][CH2:62][NH:61][CH2:60][CH2:59]2)[CH:56]=1

Participants

3

Reactant 2

HCID 118060277tert-butyl 4-((4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate2×HCID 1180606356-fluoro-1-(phenylsulfonyl)-3-(1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl)-1H-indole

Product 1

HCID 1180602855,6-difluoro-1-(phenylsulfonyl)-3-(1-(piperidin-4-ylmethyl)-1H-pyrazol-4-yl)-1H-indoleYield 308.2%

Procedure

Following the general method as outlined in Intermediate 21, starting from tert-butyl 4-((4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylate (Intermediate 45; 330 mg; 0.59 mmol), 830 mg (>100%) of the title compound was obtained as a yellow solid, which was used directly without further purification.

Sources & evidence

ORD record
ord-d8f57c9268074791a3ed1d3bafa5575a
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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