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

HRID 2274790Notes

Reaction equation

HRID 2274790 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([CH2:25][CH:26]4[CH2:31][CH2:30][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:28][CH2:27]4)[CH:24]=3)=[CH:7][N:8]2[S:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.Cl.[F:40]C1C=C2C(=CC=1F)N(S(C1C=CC=CC=1)(=O)=O)C=C2C1C=NNC=1>>[F:40][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[F:1])[N:8]([S:11]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)(=[O:12])=[O:13])[CH:7]=[C:6]2[C:20]1[CH:21]=[N:22][N:23]([CH2:25][CH:26]2[CH2:27][CH2:28][N:29]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:30][CH2:31]2)[CH:24]=1

Participants

3

Reactant 2

HCID 118060320tert-butyl 4-((4-(6-fluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylateHCID 1180603885,6-difluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole hydrochloride2×

Product 1

HCID 118060277tert-butyl 4-((4-(5,6-difluoro-1-(phenylsulfonyl)-1H-indol-3-yl)-1H-pyrazol-1-yl)methyl)piperidine-1-carboxylateYield 78%

Procedure

Following the general method as outlined in Intermediate 20, starting from 5,6-difluoro-1-(phenylsulfonyl)-3-(1H-pyrazol-4-yl)-1H-indole hydrochloride (Intermediate 30; 300 mg; 0.76 mmol), 330 mg (78%) of the title compound was obtained as a yellow solid after purification by a silica gel chromatography(petroleum ether/EtOAc=5/1).

Sources & evidence

ORD record
ord-5751401c92464da7aa6414e0fea4cf8d
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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