3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine → 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

HRID 2046919Notes

Reaction equation

HRID 2046919 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:10]([CH:11]([C:13]3[C:18]([Cl:19])=[CH:17][CH:16]=[C:15]([F:20])[C:14]=3[Cl:21])[CH3:12])=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.ClC1C=CC=C(Cl)C=1C(C1C2C(=NC=C([C:41]3[CH:42]=[N:43][N:44]([CH:46]4[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]4)[CH:45]=3)C=2)NC=1)C>>[Cl:21][C:14]1[C:15]([F:20])=[CH:16][CH:17]=[C:18]([Cl:19])[C:13]=1[CH:11]([C:10]1[C:4]2[C:5](=[N:6][CH:7]=[C:2]([C:41]3[CH:42]=[N:43][N:44]([CH:46]4[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]4)[CH:45]=3)[CH:3]=2)[NH:8][CH:9]=1)[CH3:12]

Participants

3

Reactant 2

HCID 462152983-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridineHCID 584314405-Bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine

Product 1

HCID 461964113-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Procedure

Prepared from 5-bromo-3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-1H-pyrrolo[2,3-b]-pyridine according to typical Suzuki coupling procedure described for synthesis of 3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine in example 1. MS (ES+): m/z 458.01, 460.03 [MH+]. HPLC: tR=2.34 min (ZQ3, polar—5 min).

Workup

  1. custom5 min

Sources & evidence

ORD record
ord-5cdd1a165af9456aba19acdc865c2d15
Source dataset
uspto-grants-2013_11
Patent number
US08592448B2

Reaction notes

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