Diisopropylethylamine → Ethyl 3-{[6-(acetylamino)pyridin-3-yl]ethynyl}-4-methylbenzoate

HRID 1527891Notes

Reaction equation

I[C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=1[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6].[C:14]([C:16]1[CH:17]=[CH:18][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[N:20][CH:21]=1)#[CH:15].C(N(CC)C(C)C)(C)C>CN(C=O)C.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.[Cu]I>[C:23]([NH:22][C:19]1[N:20]=[CH:21][C:16]([C:14]#[C:15][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][C:12]=2[CH3:13])[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[CH:17][CH:18]=1)(=[O:25])[CH3:24]

Participants

Conditions

Temperature: 55 °C

Procedure

A mixture of ethyl 3-iodo-4-methylbenzoate (845 mg, 2.9 mmol, 0.8 eq), N-(5-ethynylpyridin-2-yl)acetamide (3.5 mmol, 1.0 eq), Pd(PPh3)4 (51 mg, 0.044 mmol), CuI (20.4 mg, 0.11 mmol), and N,N-diisopropylethylamine (0.8 ml, 4.4 mmol) in 2 ml of DMF is heated at 55° C. (oil bath) for 1 hr under nitrogen. After cooling to r.t., the solvent is evaporated and DCM is added to dissolve the residue. The solution is washed with water and brine, dried and evaporated and the crude material is chromatographed with CombiFlash (DCM/MeOH).

Workup

temperatureAfter cooling to r.t.
customthe solvent is evaporated
additionDCM is added
dissolutionto dissolve the residue
washThe solution is washed with water and brine
customdried
customevaporated
customthe crude material is chromatographed with CombiFlash (DCM/MeOH)

Sources & evidence

ORD record: ord-b969ed8d8a014035b382aed496a0759a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090561B2

Reaction notes

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