4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → HCID 53235289, compound

HRID 1949941Notes

Reaction equation

HRID 1949941 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:14][CH2:13][CH2:12][C:11]3[S:10][C:9]([N:15]4[C:19]([CH:20]([CH3:22])[CH3:21])=[N:18][CH:17]=[N:16]4)=[N:8][C:7]=3[C:6]=2[CH:23]=1.CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][NH:35][CH:36]=2)O1>>[CH:20]([C:19]1[N:15]([C:9]2[S:10][C:11]3[CH2:12][CH2:13][O:14][C:5]4[CH:4]=[CH:3][C:2]([C:32]5[CH:33]=[N:34][NH:35][CH:36]=5)=[CH:23][C:6]=4[C:7]=3[N:8]=2)[N:16]=[CH:17][N:18]=1)([CH3:22])[CH3:21]

Participants

3

Reactant 2

HCID 27740104-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 57900383HCID 57900383, compound

Product 1

HCID 53235289HCID 53235289, compound

Procedure

Following the procedure for 484, Step 4, 9-bromo-2-(5-isopropyl-[1,2,4]triazol-1-yl)-4,5-dihydro-6-oxa-3-thia-1-aza-benzo[e]azulene was reacted with 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole to afford 489 as a white solid. LCMS (Method C): RT=10.17 min, [M+H]+=379. 1H NMR (DMSO-d6): 12.95 (1 H, bs), 8.42 (1 H, d, J=2.3 Hz), 8.18 (1 H, s), 8.07 (1 H, bs), 7.81 (1 H, bs), 7.51 (1 H, dd, J=8.3, 2.3 Hz), 7.06 (1 H, d, J=8.3 Hz), 4.36 (2 H, t, J=5.0 Hz), 4.12-4.04 (1 H, m), 3.38 (2 H, t, J=5.0 Hz), 1.47 (3 H, s), 1.46 (3 H, s).

Sources & evidence

ORD record
ord-cdfdf4b6839746ef80e2501c2d8e412f
Source dataset
uspto-grants-2013_03
Patent number
US08399690B2

Reaction notes

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