tert-butyl N-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]carbamate → 8-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-one

HRID 1853890Notes

Reaction equation

HRID 1853890 reaction equation
Br[C:2]1[C:3]2[C:4]3[CH:23]=[CH:22][S:21][C:5]=3[C:6](=[O:20])[NH:7][C:8]=2[CH:9]=[CH:10][C:11]=1[O:12][Si](C(C)(C)C)(C)C.CC1(C)C(C)(C)OB([C:32]2[CH2:37][CH2:36][CH:35]([NH:38][C:39](=O)OC(C)(C)C)CC=2)O1>>[OH:12][C:11]1[CH:10]=[CH:9][C:8]2[NH:7][C:6](=[O:20])[C:5]3[S:21][CH:22]=[CH:23][C:4]=3[C:3]=2[C:2]=1[C:37]1[CH2:32][CH2:39][NH:38][CH2:35][CH:36]=1

Participants

3

Reactant 2

HCID 66570714tert-butyl N-[4-(tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl]carbamateHCID 674481399-Bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one

Product 1

HCID 534727628-Hydroxy-9-(1,2,3,6-tetrahydropyridin-4-yl)thieno[2,3-c]quinolin-4(5H)-oneYield 234.6%

Procedure

Following General Procedure B, 9-bromo-8-(tert-butyldimethylsilyloxy)thieno[2,3-c]quinolin-4(5H)-one (80 mg, 0.20 mmol) was reacted with tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-enylcarbamate (90 mg, 0.29 mmol) to afford the desired product (140 mg, 23%) as an off-white solid: 1H NMR (500 MHz, CD3OD) δ 8.01-7.98 (m, 2H), 7.35 (d, J=8.9 Hz, 1H), 7.12 (d, J=8.9 Hz, 1H), 5.80 (s, 1H), 4.01-3.91 (m, 2H), 3.63-3.60 (m, 2H), 2.88-2.84 (m, 1H), 2.57-2.53 (m, 1H); ESI MS m/z 299 [C16H14N2O2S+H]+; HPLC >99% (AUC), tR=6.70 min.

Sources & evidence

ORD record
ord-8994e4aa942c4bfba4248252c96df963
Source dataset
uspto-grants-2015_02
Patent number
US08962648B2

Reaction notes

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