3-Bromobenzonitrile → HCID 11644132, compound

HRID 970337Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[NH:10]1[CH2:15][CH2:14][S:13][CH2:12][CH2:11]1.CC([O-])(C)C.[Na+]>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].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1>[N:10]1([C:2]2[CH:3]=[C:4]([CH:7]=[CH:8][CH:9]=2)[C:5]#[N:6])[CH2:15][CH2:14][S:13][CH2:12][CH2:11]1

Participants

Conditions

Temperature: 85 °C

Procedure

A 10 dram vial was charged with 3-bromo-benzonitrile (280 mg, 1.54 mmol), thiomorpholine (190 mg, 1.85 mmol), NaOtBu (207 mg, 2.15 mmol), BINAP (14.4 mg, 0.023 mmol), toluene (3 mL), Pd2(dba)3 (7 mg, 0.0077 mmol), and flushed with argon. The reaction mixture was heated to 85° C. for 48 h, and then cooled to RT. The resulting mixture was diluted with Et2O (10 mL), filtered through celite, and washed with Et2O (7 mL) two times. The filtrate was concentrated in vacuo and purified by silica gel chromatography (20% EtOAC/Hexane) to give compound 387A as a yellow oil (256 mg). HPLC retention time=2.48 min. (Condition A), M+=205.

Workup

customflushed with argon
temperaturecooled to RT
additionThe resulting mixture was diluted with Et2O (10 mL)
filtrationfiltered through celite
washwashed with Et2O (7 mL) two times
concentrationThe filtrate was concentrated in vacuo
custompurified by silica gel chromatography (20% EtOAC/Hexane)

Sources & evidence

ORD record: ord-837b9e79cfe14c15965c267c56f46c9b
Source dataset: uspto-grants-2007_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07312209B2

Reaction notes

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