1-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → tert-butyl 4-((2-(5-fluoro-1H-indol-4-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate

HRID 2091884Notes

Reaction equation

HRID 2091884 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:26]2[CH2:31][CH2:30][O:29][CH2:28][CH2:27]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Si]([N:39]1[C:47]2[C:42](=[C:43](B3OC(C)(C)C(C)(C)O3)[C:44]([F:48])=[CH:45][CH:46]=2)[CH:41]=[CH:40]1)(C(C)(C)C)(C)C>>[F:48][C:44]1[C:43]([C:2]2[N:3]=[C:4]([N:26]3[CH2:31][CH2:30][O:29][CH2:28][CH2:27]3)[C:5]3[N:11]=[C:10]([CH2:12][CH:13]4[CH2:18][CH2:17][N:16]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:15][CH2:14]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)=[C:42]2[C:47](=[CH:46][CH:45]=1)[NH:39][CH:40]=[CH:41]2

Participants

3

Reactant 2

HCID 575067251-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indoleHCID 58404998Tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate

Product 1

HCID 53378677tert-butyl 4-((2-(5-fluoro-1H-indol-4-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate

Procedure

tert-butyl 4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidine-1-carboxylate (0.2 g) 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 and purified via reverse phase hplc to produce 57.5 mg of 137. MS (Q1) 547.3 (M)+

Workup

  1. custompurified via reverse phase hplc

Sources & evidence

ORD record
ord-09fb707781c5413996bc81a035cf1755
Source dataset
uspto-grants-2013_05
Patent number
US08440651B2

Reaction notes

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