2-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine → 6-fluoro-1-(phenylsulfonyl)-3-(1-(pyridin-2-yl)-1H-pyrazol-4-yl)-1H-indole

HRID 2274764Notes

Reaction equation

HRID 2274764 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](C4C=CN=CC=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.CC1(C)C(C)(C)OB(C2C=NN([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=3)C=2)O1>>[F:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:20]3[CH:21]=[N:22][N:23]([C:44]4[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=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:12])=[O:13])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 665212452-(4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine2×HCID 1180602116-fluoro-1-(phenylsulfonyl)-3-(1-(pyridin-4-yl)-1H-pyrazol-4-yl)-1H-indole

Product 1

HCID 1180606196-fluoro-1-(phenylsulfonyl)-3-(1-(pyridin-2-yl)-1H-pyrazol-4-yl)-1H-indoleYield 62%

Procedure

Following the general method as outlined in Intermediate 10, starting from 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)pyridine (Intermediate 14; 485 mg; 1.80 mmol), 234 mg (62%) of the title compound was obtained as a yellow solid after purification by a silica gel chromatography (petroleum ether/EtOAc=1/1).

Sources & evidence

ORD record
ord-1f856f88510543bc8e30783e7c61cb27
Source dataset
uspto-grants-2015_09
Patent number
US09126984B2

Reaction notes

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