1-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 4-(6-((3-(4,4-difluoropiperidin-1-yl)azetidin-1-yl)methyl)-2-(5-fluoro-1H-indol-4-yl)pyrido[3,2-d]pyrimidin-4-yl)morpholine

HRID 1043594Notes

Reaction equation

HRID 1043594 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:25]2[CH2:30][CH2:29][O:28][CH2:27][CH2:26]2)[C:5]2[N:11]=[C:10]([CH2:12][N:13]3[CH2:16][CH:15]([N:17]4[CH2:22][CH2:21][C:20]([F:24])([F:23])[CH2:19][CH2:18]4)[CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Si]([N:38]1[C:46]2[C:41](=[C:42](B3OC(C)(C)C(C)(C)O3)[C:43]([F:47])=[CH:44][CH:45]=2)[CH:40]=[CH:39]1)(C(C)(C)C)(C)C>>[F:23][C:20]1([F:24])[CH2:21][CH2:22][N:17]([CH:15]2[CH2:16][N:13]([CH2:12][C:10]3[CH:9]=[CH:8][C:6]4[N:7]=[C:2]([C:42]5[C:43]([F:47])=[CH:44][CH:45]=[C:46]6[C:41]=5[CH:40]=[CH:39][NH:38]6)[N:3]=[C:4]([N:25]5[CH2:30][CH2:29][O:28][CH2:27][CH2:26]5)[C:5]=4[N:11]=3)[CH2:14]2)[CH2:18][CH2:19]1

Participants

3

Reactant 2

HCID 575067251-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 584050374-(2-Chloro-6-((3-(4,4-difluoropiperidin-1-yl)azetidin-1-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine

Product 1

HCID 533784694-(6-((3-(4,4-difluoropiperidin-1-yl)azetidin-1-yl)methyl)-2-(5-fluoro-1H-indol-4-yl)pyrido[3,2-d]pyrimidin-4-yl)morpholine

Procedure

4-(2-chloro-6-((3-(4,4-difluoropiperidin-1-yl)azetidin-1-yl)methyl)pyrido[3,2-d]pyrimidin-4-yl)morpholine was reacted with 1-(tert-butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole via General Procedure A to produce 24.7 mg of 125 following reverse phase HPLC purification. MS (Q1) 538.3 (M)+

Workup

  1. customto produce
  2. custom24.7 mg of 125 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-e521927949d24f448c64d2ebd2a65622
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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