3-(4-Fluorophenoxy)benzyl Bromide → 1-{[3-(4-fluorophenoxy)benzyl]oxy}-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridine

HRID 1404601Notes

Reaction equation

HRID 1404601 reaction equation
[OH:1][N:2]1[C:10]2[C:5](=[N:6][CH:7]=[C:8]([C:11]3[CH:12]=[N:13][N:14]([CH:16]4[CH2:21][CH2:20][N:19](C(OC(C)(C)C)=O)[CH2:18][CH2:17]4)[CH:15]=3)[CH:9]=2)[CH:4]=[CH:3]1.Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([O:37][C:38]2[CH:43]=[CH:42][C:41]([F:44])=[CH:40][CH:39]=2)[CH:32]=1>>[F:44][C:41]1[CH:42]=[CH:43][C:38]([O:37][C:33]2[CH:32]=[C:31]([CH:36]=[CH:35][CH:34]=2)[CH2:30][O:1][N:2]2[C:10]3[C:5](=[N:6][CH:7]=[C:8]([C:11]4[CH:12]=[N:13][N:14]([CH:16]5[CH2:17][CH2:18][NH:19][CH2:20][CH2:21]5)[CH:15]=4)[CH:9]=3)[CH:4]=[CH:3]2)=[CH:39][CH:40]=1

Participants

3

Reactant 2

HCID 27374563-(4-Fluorophenoxy)benzyl BromideHCID 67458749tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate

Product 1

HCID 585323071-{[3-(4-fluorophenoxy)benzyl]oxy}-6-[1-(piperidin-4-yl)-1H-pyrazol-4-yl]-1H-pyrrolo[3,2-b]pyridine

Procedure

The entitled compound is prepared from tert-butyl 4-[4-(1-hydroxy-1H-pyrrolo[3,2-b]pyridin-6-yl)-1H-pyrazol-1-yl]piperidine-1-carboxylate and 1-(bromomethyl)-3-(4-fluorophenoxy)benzene as described in the last 2 steps of Example 18.

Sources & evidence

ORD record
ord-df078f6e53b24c7d98f5205a54bc91d8
Source dataset
uspto-grants-2014_12
Patent number
US08912330B2

Reaction notes

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