2-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-ol → HCID 58203765, compound

HRID 1849329Notes

Reaction equation

HRID 1849329 reaction equation
[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[CH:8][N:7]=[C:6]2[C:10]2[S:11][C:12]3[CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22](Br)[CH:21]=[CH:20][C:17]=4[C:18]=3[N:19]=2)[CH2:2]1.[CH3:25][C:26]([OH:43])([CH3:42])[CH2:27][N:28]1[CH:32]=[C:31](B2OC(C)(C)C(C)(C)O2)[CH:30]=[N:29]1>[Pd]>[NH:1]1[CH2:4][CH:3]([N:5]2[CH:9]=[CH:8][N:7]=[C:6]2[C:10]2[S:11][C:12]3[CH2:13][CH2:14][O:15][C:16]4[CH:23]=[C:22]([C:31]5[CH:30]=[N:29][N:28]([CH2:27][C:26]([CH3:42])([OH:43])[CH3:25])[CH:32]=5)[CH:21]=[CH:20][C:17]=4[C:18]=3[N:19]=2)[CH2:2]1

Participants

4

Reactant 2

HCID 582041312-methyl-1-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]propan-2-olHCID 86652323HCID 86652323, compound

Product 1

HCID 58203765HCID 58203765, compound

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Following the procedure for 355, 2-(1-Azetidin-3-yl-1H-imidazol-2-yl)-8-bromo-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene and 2-methyl-1-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)propan-2-ol were reacted under Suzuki palladium conditions to give 411. MS: (ESI+)=463.2. 1H NMR (400 MHz, DMSO) δ 8.36 (d, J=8.2 Hz, 1H), 8.15 (s, 1H), 7.94 (s, 1H), 7.84 (s, 1H), 7.45 (dd, J=8.3, 1.7 Hz, 1H), 7.28 (d, J=1.7 Hz, 1H), 7.14 (s, 1H), 6.16-6.06 (m, 1H), 4.72 (s, 1H), 4.36 (t, J=5.0 Hz, 2H), 4.04 (s, 2H), 3.98 (t, J=8.2 Hz, 2H), 3.82-3.76 (m, 2H), 1.10 (s, 6H)

Sources & evidence

ORD record
ord-b61d3bad89584ab3a591ae29bae0ecbd
Source dataset
uspto-grants-2015_02
Patent number
US08952043B2

Reaction notes

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