Dichloromethane → 5-Cyclopropylnicotinonitrile

HRID 717543Notes

Reaction equation

C(=O)([O-])[O-].[Cs+].[Cs+].Br[C:8]1[CH:9]=[N:10][CH:11]=[C:12]([CH:15]=1)[C:13]#[N:14].[CH:16]1(B(O)O)[CH2:18][CH2:17]1.C(Cl)Cl>O1CCOCC1.O>[CH:16]1([C:8]2[CH:9]=[N:10][CH:11]=[C:12]([CH:15]=2)[C:13]#[N:14])[CH2:18][CH2:17]1

Participants

Conditions

Temperature: 100 °C

Procedure

Cesium carbonate (20.8 g, 0.064 mol) was added to a stirred solution of 5-bromonicotinonitrile (6 g, 0.0322 mol) and cyclopropylboronic acid (2.8 g, 0.032 mol) in a mixture of 1,4-dioxan (100 mL) and water (50 mL). The reaction vessel was purged with argon for 20 min and Pd(dppf)2Cl2.DCM (1.3 g, 0.0016 mol) was added to the reaction mixture. The reaction vessel was purged again with argon for 10 min and subsequently allowed to stir at 100° C. for 3 h. The reaction mixture was filtered through a filter bed of CELITE and the filter bed was thoroughly washed with ethyl acetate (3×200 mL). The collected organic fractions were concentrated under vacuum to afford the crude product, which was purified by silica gel column chromatography to afford 5-cyclopropylnicotinonitrile. MS (M+1): 144.8.

Workup

customThe reaction vessel was purged with argon for 20 min
customThe reaction vessel was purged again with argon for 10 min
filtrationThe reaction mixture was filtered through a filter bed of CELITE
washthe filter bed was thoroughly washed with ethyl acetate (3×200 mL)
concentrationThe collected organic fractions were concentrated under vacuum
customto afford the crude product, which
customwas purified by silica gel column chromatography

Sources & evidence

ORD record: ord-0c5065dceb274b0ca0f06e8f580cd736
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193724B2

Reaction notes

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