5-Chloro-1H-pyrrolo[2,3-b]pyridine → [2-chloro-6-fluoro-3-(2-methoxy-ethoxy)-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

HRID 253446Notes

Reaction equation

HRID 253446 reaction equation
[Cl:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:8][CH:7]=[C:6]([F:15])[C:3]=1[CH:4]=[O:5].ClC1C(OCC(F)(F)F)=CC=C(Cl)C=1C(C1C2C(=NC=C(C3C=NN(C)C=3)C=2)NC=1)O.[Cl:47][C:48]1[CH:49]=[C:50]2[CH:56]=[CH:55][NH:54][C:51]2=[N:52][CH:53]=1>>[Cl:1][C:2]1[C:9]([O:10][CH2:11][CH2:12][O:13][CH3:14])=[CH:8][CH:7]=[C:6]([F:15])[C:3]=1[C:4]([C:56]1[C:50]2[C:51](=[N:52][CH:53]=[C:48]([Cl:47])[CH:49]=2)[NH:54][CH:55]=1)=[O:5]

Participants

4

Reactant 3

HCID 242292135-Chloro-1H-pyrrolo[2,3-b]pyridineHCID 598038162-Chloro-6-fluoro-3-(2-methoxy-ethoxy)-benzaldehydeHCID 59803863[2,6-dichloro-3-(2,2,2-trifluoro-ethoxy)-phenyl]-[5-(1-methyl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-methanol

Product 1

HCID 24954129[2-chloro-6-fluoro-3-(2-methoxy-ethoxy)-phenyl]-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-methanone

Procedure

Additional compounds were prepared using the protocol of Scheme 41, optionally substituting 2-chloro-6-fluoro-3-(2-methoxy-ethoxy)-benzaldehyde 123 with a suitable aldehyde (prepared as described in Examples 36, 39 or 40), and/or optionally replacing 5-chloro-1H-pyrrolo[2,3-b]pyridine 4 with an appropriate substituted 7-azaindole (5-methoxy-7-azaindole per Example 8, 5-(1-methyl-1H-pyrazol-4-yl)-7-azaindole per Example 35) in Step 1. The following compounds were made following this procedure:

Workup

  1. customAdditional compounds were prepared

Sources & evidence

ORD record
ord-f9bee0ce16a24c73b221395dd71876ff
Source dataset
uspto-grants-2011_01
Patent number
US07872018B2

Reaction notes

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