Phenylboronic Acid → HCID 67064835, compound

HRID 1409139Notes

Reaction equation

Cl[C:2]1[N:7]2[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]2[N:5]=[C:4]([NH:12][C:13](=[O:25])[C:14]2[CH:19]=[CH:18][C:17]([C:20]([CH3:24])([CH3:23])[CH2:21][OH:22])=[CH:16][CH:15]=2)[CH:3]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[OH:22][CH2:21][C:20]([C:17]1[CH:18]=[CH:19][C:14]([C:13]([NH:12][C:4]2[CH:3]=[C:2]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[N:7]3[N:8]=[C:9]([CH3:11])[CH:10]=[C:6]3[N:5]=2)=[O:25])=[CH:15][CH:16]=1)([CH3:24])[CH3:23]

Participants

Conditions

Temperature: 110 °C

Procedure

A suspension of N-(7-chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-yl)-4-(1-hydroxy-2-methylpropan-2-yl)benzamide (4G, 44 mg, 1.0 equivalent), phenylboronic acid (1.5 equivalents) and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.09 equivalents) in 2:1 dioxane/saturated aqueous NaHCO3 (0.125 M with respect to 4G) was warmed to 110° C. in a microwave reactor. The reaction mixture was cooled to room temperature, diluted with methanol, filtered, and purified via preparative HPLC to afford the title compound (49%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.26 (s, 6H), 2.40 (s, 3H), 3.47 (s, 2H), 4.76 (br. s., 1H), 6.40 (s, 1H), 7.53 (d, J=8.59 Hz, 2H), 7.58-7.68 (m, 3H), 7.94-8.04 (m, 3H), 8.04-8.10 (m, 2H), 11.19 (s, 1H). ESI-MS: m/z 401.1 (M+H)+.

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered
custompurified via preparative HPLC

Sources & evidence

ORD record: ord-690fac4003c8416b9e77658549179ee6
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08921358B2

Reaction notes

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