4-Hydroxyphenylboronic acid → HCID 178515847, compound

HRID 1672472Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([NH:12][C@H:13]1[CH2:18][CH2:17][C@H:16]([OH:19])[CH2:15][CH2:14]1)[N:8]=[CH:7]2.[OH:20][C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CN(C=O)C>[OH:19][C@H:16]1[CH2:17][CH2:18][C@H:13]([NH:12][C:9]2[N:8]=[CH:7][C:6]3[C:11](=[C:2]([C:24]4[CH:25]=[CH:26][C:21]([OH:20])=[CH:22][CH:23]=4)[CH:3]=[CH:4][CH:5]=3)[N:10]=2)[CH2:14][CH2:15]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a flask charged with trans-4-[(8-bromoquinazolin-2-yl)amino]cyclohexanol (1.3 g, 4.035 mmol) was added Pd(PPh3)4 (233 mg, 0.202 mmol), K3PO4.3H2O (2.686 mg, 10.09 mmol), 4-hydroxybenzeneboronic acid (1.113 g, 8.07 mmol) and DMF (16 mL) under argon. The mixture was heated at 80-90° C. under argon overnight, then cooled to room temperature and filtered. The filtrate was concentrated under vacuum and purified by silica gel chromatography (eluted with EA:PE=2:1) to give the title compound as a yellow solid (1 g, 74%). 1 HNMR (DMSO-d6, 400 MHz): δ 9.50 (s, 1H), 9.01 (s, 1H), 7.72-7.61 (m, 3H), 7.31-7.20 (m, 2H), 6.83 (t, 2H, J=7.6 Hz), 4.53 (d, 1H, J=4 Hz), 3.70-3.55 (m, 1H), 3.45-3.36 (m, 1H), 1.99-1.84 (m, 4H), 1.35-1.14 (m, 4H).

Workup

temperaturecooled to room temperature
filtrationfiltered
concentrationThe filtrate was concentrated under vacuum
custompurified by silica gel chromatography (eluted with EA:PE=2:1)

Sources & evidence

ORD record: ord-eb5669e8fe9b466789b26e07943405c4
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07998978B2

Reaction notes

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