Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate → (2-(2-(1H-indol-5-yl)ethyl)-5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol

HRID 340324Notes

Reaction equation

[Si]([O:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13](B2OC(C)(C)C(C)(C)O2)=[C:14]([NH:16]C(=O)OC(C)(C)C)[CH:15]=1)(C(C)(C)C)(C)C.[NH:33]1[C:41]2[C:36](=[CH:37][C:38]([C:42]#[C:43][C:44]3[CH:45]=[C:46](Cl)[C:47]([C:50]#[N:51])=[N:48][CH:49]=3)=[CH:39][CH:40]=2)[CH:35]=[CH:34]1>>[NH:33]1[C:41]2[C:36](=[CH:37][C:38]([CH2:42][CH2:43][C:44]3[CH:49]=[N:48][C:47]4[C:50]([NH2:51])=[N:16][C:14]5[CH:15]=[C:10]([CH2:9][OH:8])[CH:11]=[CH:12][C:13]=5[C:46]=4[CH:45]=3)=[CH:39][CH:40]=2)[CH:35]=[CH:34]1

Participants

Reactant 2

HCID 66890509Tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate

HCID 668923115-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile

Product 1

HCID 58213555(2-(2-(1H-indol-5-yl)ethyl)-5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol

Procedure

(2-(2-(1H-indol-5-yl)ethyl)-5-aminobenzo[f][1,7]naphthyridin-8-yl)methanol was prepared from tert-butyl 5-((tert-butyldimethylsilyloxy)methyl)-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenylcarbamate (from Example 99/step 1) and 5-((1H-indol-5-yl)ethynyl)-3-chloropicolinonitrile (from Example 44/step 3) following the procedures described for Example 44/Step 4 and Example 99/step 3 (deprotection of TBS). 1H NMR (acetone-d6): δ 10.19 (t, 1H), 8.83 (d, 1H), 8.71 (d, 1H), 8.35 (d, 1H), 7.60 (d, 1H), 7.46 (d, 1H), 7.36-7.27 (m, 3H), 7.04 (dd, 1H), 6.57 (br s, 2H), 6.38 (dt, 1H), 4.77 (d, 2H), 4.36 (t, 1H), 3.29 (t, 2H), 3.19 (t, 2H). LRMS [M+H]=369.2.

Sources & evidence

ORD record: ord-68b37e6241804aeab5e0a7b34d568c90
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08895577B2

Reaction notes

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