3-(Trifluoromethyl)aniline → 5-(6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1-naphthamide

HRID 709321Notes

Reaction equation

HRID 709321 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([O:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30](O)=[O:31])[CH:3]=1.[F:33][C:34]([F:43])([F:42])[C:35]1[CH:36]=[C:37]([NH2:41])[CH:38]=[CH:39][CH:40]=1>>[Cl:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:17])([CH3:18])[CH3:16])[CH:9]=[CH:10][C:5]2=[C:4]([O:19][C:20]2[CH:29]=[CH:28][CH:27]=[C:26]3[C:21]=2[CH:22]=[CH:23][CH:24]=[C:25]3[C:30]([NH:41][C:37]2[CH:38]=[CH:39][CH:40]=[C:35]([C:34]([F:33])([F:42])[F:43])[CH:36]=2)=[O:31])[CH:3]=1

Participants

3

Reactant 2

HCID 73753-(Trifluoromethyl)anilineHCID 86676742HCID 86676742, compound

Product 1

HCID 866767435-(6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1-naphthamideYield 88.4%

Procedure

5-(6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-N-(3-(trifluoromethyl)phenyl)-1-naphthamide (92 mg, 88% yield) was prepared as described for Example 11-D starting from 5-(6-chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-1-naphthoic acid (80 mg, 0.17 mmol) and 3-(trifluoromethyl)benzenamine (55 mg, 0.34 mmol). MS m/z: 612 [M+1].

Sources & evidence

ORD record
ord-466753f07ba144678825ca183ae0a13b
Source dataset
uspto-grants-2015_11
Patent number
US09180127B2

Reaction notes

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