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

HRID 1043634Notes

Reaction equation

HRID 1043634 reaction equation
Cl[C:2]1[N:3]=[C:4]([N:22]2[CH2:27][CH2:26][O:25][CH2:24][CH2:23]2)[C:5]2[N:11]=[C:10]([CH2:12][CH:13]3[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]3)[CH:9]=[CH:8][C:6]=2[N:7]=1.[Si]([N:35]1[C:43]2[C:38](=[C:39](B3OC(C)(C)C(C)(C)O3)[C:40]([F:44])=[CH:41][CH:42]=2)[CH:37]=[CH:36]1)(C(C)(C)C)(C)C>>[F:44][C:40]1[C:39]([C:2]2[N:3]=[C:4]([N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)[C:5]3[N:11]=[C:10]([CH2:12][CH:13]4[CH2:18][CH2:17][N:16]([C:19](=[O:21])[CH3:20])[CH2:15][CH2:14]4)[CH:9]=[CH:8][C:6]=3[N:7]=2)=[C:38]2[C:43](=[CH:42][CH:41]=1)[NH:35][CH:36]=[CH:37]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 584049991-(4-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone

Product 1

HCID 533789021-(4-((2-(5-fluoro-1H-indol-4-yl)-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone

Procedure

1-(4-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-1-yl)ethanone (30 mg) 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 13.7 mg of 148 following reverse phase HPLC purification. MS (Q1) 489.2 (M)+

Workup

  1. customto produce
  2. custom13.7 mg of 148 following reverse phase HPLC purification

Sources & evidence

ORD record
ord-7e591853f0b44869bc5aab0bacf8ba56
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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