1-(tert-Butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole → 2-(1-{[2-(5-Fluoro-1h-Indol-4-Yl)-4-(Morpholin-4-Yl)pyrido[3,2-D]pyrimidin-6-Yl]methyl}piperidin-4-Yl)propan-2-Ol

HRID 1043566Notes

Reaction equation

HRID 1043566 reaction equation
[Si]([N:8]1[C:16]2[C:11](=[C:12](B3OC(C)(C)C(C)(C)O3)[C:13]([F:17])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)(C(C)(C)C)(C)C.Cl[C:28]1[N:29]=[C:30]([N:49]2[CH2:54][CH2:53][O:52][CH2:51][CH2:50]2)[C:31]2[N:37]=[C:36]([CH2:38][N:39]3[CH2:44][CH2:43][CH:42]([C:45]([OH:48])([CH3:47])[CH3:46])[CH2:41][CH2:40]3)[CH:35]=[CH:34][C:32]=2[N:33]=1>>[F:17][C:13]1[C:12]([C:28]2[N:29]=[C:30]([N:49]3[CH2:54][CH2:53][O:52][CH2:51][CH2:50]3)[C:31]3[N:37]=[C:36]([CH2:38][N:39]4[CH2:44][CH2:43][CH:42]([C:45]([OH:48])([CH3:47])[CH3:46])[CH2:41][CH2:40]4)[CH:35]=[CH:34][C:32]=3[N:33]=2)=[C:11]2[C:16](=[CH:15][CH:14]=1)[NH:8][CH:9]=[CH:10]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 584049702-(1-((2-Chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol

Product 1

HCID 533780512-(1-{[2-(5-Fluoro-1h-Indol-4-Yl)-4-(Morpholin-4-Yl)pyrido[3,2-D]pyrimidin-6-Yl]methyl}piperidin-4-Yl)propan-2-Ol

Procedure

Following General Procedure A, 1-(tert-butyldimethylsilyl)-5-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole and 2-(1-((2-chloro-4-morpholinopyrido[3,2-d]pyrimidin-6-yl)methyl)piperidin-4-yl)propan-2-ol from Example 8 were reacted to give 105. LCMS (MH+)=505.2. 1H-NMR (DMSO-d6): δ 11.2 (s, 1H), 8.15 (d, 1H), 7.87 (d, 1H), 7.47 (m, 1H), 7.44 (s, 1H), 7.01 (m, 1H), 6.75 (s, 1H), 4.49 (s, 4H), 4.02 (s, 1H), 3.80 (m, 4H), 3.73 (s, 2H), 2.93 (m, 2H), 1.99 (m, 2H), 1.66 (m, 2H), 1.28 (m, 3H), 1.04 (s, 6H)

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-1688917e13bb43229249badaf4d18a88
Source dataset
uspto-grants-2013_10
Patent number
US08563540B2

Reaction notes

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