1-(2-Morpholinoethyl)-1H-pyrazole-4-boronic acid pinacol ester → HCID 58203989, compound

HRID 707870Notes

Reaction equation

HRID 707870 reaction equation
Br[C:2]1[CH:25]=[CH:24][C:5]2[C:6]3[N:7]=[C:8]([C:14]4[N:15]([CH2:19][C:20]([F:23])([F:22])[F:21])[N:16]=[CH:17][N:18]=4)[S:9][C:10]=3[CH2:11][CH2:12][O:13][C:4]=2[CH:3]=1.CC1(C)C(C)(C)OB([C:34]2[CH:35]=[N:36][N:37]([CH2:39][CH2:40][N:41]3[CH2:46][CH2:45][O:44][CH2:43][CH2:42]3)[CH:38]=2)O1>>[N:41]1([CH2:40][CH2:39][N:37]2[CH:38]=[C:34]([C:25]3[CH:2]=[CH:3][C:4]4[O:13][CH2:12][CH2:11][C:10]5[S:9][C:8]([C:14]6[N:15]([CH2:19][C:20]([F:21])([F:22])[F:23])[N:16]=[CH:17][N:18]=6)=[N:7][C:6]=5[C:5]=4[CH:24]=3)[CH:35]=[N:36]2)[CH2:42][CH2:43][O:44][CH2:45][CH2:46]1

Participants

3

Reactant 2

HCID 177499241-(2-Morpholinoethyl)-1H-pyrazole-4-boronic acid pinacol esterHCID 582038498-Bromo-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene

Product 1

HCID 58203989HCID 58203989, compoundYield 17%

Procedure

8-Bromo-2-[2-(2,2,2-trifluoro-ethyl)-2H-[1,2,4]triazol-3-yl]-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethyl)morpholine were reacted under palladium Suzuki conditions to give 115 (17% yield). LC/MS (ESI+): m/z 532 (M+H). 1H NMR (400 MHz, DMSO) δ 8.48 (d, J=2.1, OH), 8.30 (s, OH), 8.07 (s, OH), 7.76 (s, OH), 7.49 (dd, J=8.3, 2.2, OH), 7.09 (d, J=8.3, OH), 5.89 (q, J=8.6, OH), 4.38 (t, J=4.9, OH), 4.25 (t, J=6.6, OH), 3.61-3.51 (m, 1H), 3.48 (t, J=4.9, OH), 2.75 (t, J=6.6, OH), 2.45-2.35 (m, 1H)

Sources & evidence

ORD record
ord-96d21b39b2844197aaa8aed7c7e5f7e8
Source dataset
uspto-grants-2015_11
Patent number
US09175009B2

Reaction notes

Loading…