2-Methoxyphenylboronic acid → 4-[3-(2-Methoxy-phenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-piperazine-1-carboxylic acid isopropyl ester

HRID 1844347Notes

Reaction equation

HRID 1844347 reaction equation
[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21](Br)=[C:15]3[N:14]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][C:26]=1B(O)O>>[CH:1]([O:4][C:5]([N:7]1[CH2:12][CH2:11][N:10]([C:13]2[CH:18]=[CH:17][N:16]3[N:19]=[CH:20][C:21]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][C:25]=4[O:24][CH3:23])=[C:15]3[N:14]=2)[CH2:9][CH2:8]1)=[O:6])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 27339582-Methoxyphenylboronic acidHCID 86697433Isopropyl 4-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)piperazine-1-carboxylate

Product 1

HCID 866974354-[3-(2-Methoxy-phenyl)-pyrazolo[1,5-a]pyrimidin-5-yl]-piperazine-1-carboxylic acid isopropyl esterYield 17.6%

Procedure

Prepared similarly to the preparation of example 5.6.9 from 4-(3-bromo-pyrazolo[1,5-a]pyrimidin-5-yl)-piperazine-1-carboxylic acid isopropyl ester (385.0 mg, 1.1 mmol) and 2-methoxyphenylboronic acid [5720-06-9] (191.8 mg, 1.3 mmol) to afford 76.4 mg of yellow powder as a free base, mp. 57-59° C. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.22 (d, J=6.32 Hz, 6 H) 3.48-3.54 (m, 4 H) 3.68-3.77 (m, 4 H) 3.87 (s, 3 H) 4.77-4.85 (m, 1 H) 6.76 (d, J=7.83 Hz, 1 H) 6.94-7.07 (m, 2 H) 7.10-7.18 (m, 1 H) 8.38 (dd, J=7.71, 1.64 Hz, 1 H) 8.43 (s, 1 H) 8.71 (d, J=8.08 Hz, 1 H). 13C NMR (100 MHz, DMSO-d6) δ ppm 21.95, 44.07, 55.32, 68.14, 96.93, 101.10, 111.29, 120.48, 121.64, 125.83, 127.67, 136.28, 145.00, 154.31, 155.25, 155.51. LRMS (ESI) m/z 396.1 [(M+H)]+, calc'd for C21H26N6O3: 395.47.

Sources & evidence

ORD record
ord-f9414cda7a7e43d8b14d717f8fb95425
Source dataset
uspto-grants-2015_02
Patent number
US08946415B2

Reaction notes

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