3-Bromobenzonitrile → HCID 67517884, compound

HRID 1808740Notes

Reaction equation

C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1)(C)(C)C.CC(C)([O-])C.[Na+].Br[C:29]1[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=1)[C:32]#[N:33].[OH:37][CH:38]1[CH2:43][CH2:42][NH:41][CH2:40][CH2:39]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[OH:37][CH:38]1[CH2:43][CH2:42][N:41]([C:29]2[CH:30]=[C:31]([CH:34]=[CH:35][CH:36]=2)[C:32]#[N:33])[CH2:40][CH2:39]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a toluene (140 mL) suspension of tris(dibenzylideneacetone)dipalladium (2.06 g, 2.25 mmol), 2-(di-tert-butylphosphino)biphenyl (0.839 g, 2.81 mmol), sodium tert-butoxide (4.05 g, 42.2 mmol) was added 3-bromobenzonitrile (5.11 g, 28.1 mmol), followed by 4-hydroxypiperidine (2.84 g, 28.1 mmol). The reaction mixture was heated to 80° C. for 5 hours while stirring under nitrogen. It was allowed to cool to room temperature, filtered, and concentrated in vacuo. Chromatography over silica gel, eluting with hexanes/ethyl acetate, afforded the title compound. 1H NMR (500 MHz, CDCl3) δ 7.33-7.24 (m, 1H), 7.15-7.10 (m, 2H), 7.06 (d, J=7.5 Hz, 1H), 3.95-3.87 (m, 1H), 3.57 (dt, J=12.7, 4.8 Hz, 2H), 3.00 (ddd, J=12.8, 9.5, 3.2 Hz, 2H), 2.05-1.95 (m, 2H), 1.73-1.59 (m, 2H); LC-MS: m/z 203.2 (M+H).

Workup

temperatureto cool to room temperature
filtrationfiltered
concentrationconcentrated in vacuo
washChromatography over silica gel, eluting with hexanes/ethyl acetate

Sources & evidence

ORD record: ord-97fd05ebb5f2453288be51c485a0f851
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08361994B2

Reaction notes

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