Sodium Carbonate → Benzamide, N,N-bis(1-methylethyl)-

HRID 1767683Notes

Reaction equation

C[C:2]([CH3:14])([CH3:13])[C:3]([NH:5][C:6]1[CH:7]=NC=C[C:11]=1I)=[O:4].C(=O)([O-])[O-].[Na+].[Na+]>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>[CH:6]([N:5]([CH:6]([CH3:11])[CH3:7])[C:3](=[O:4])[C:2]1[CH:13]=[CH:13][CH:2]=[CH:3][CH:14]=1)([CH3:7])[CH3:11]

Participants

Conditions

Temperature: 83 °C

Procedure

Bis amide 17. The 2,2-dimethyl-N-(4-iodo-3-pyridinyl)propanamide (700 mg, 2.3 mmol) and 2-diisopropylbenzamide boronic acid (1.3 g, 5.2 mmol) were dissolved in DMF. Tetrakis(triphenylphosphine)palladium (133 mg, 0.11 mmol) and 2 M sodium carbonate solution (2.2 mL) were added. The reaction was refluxed at 83° C. for 18 h The mixture was concentrated in vacuo, extracted with EtOAc, washed with brine and dried with sodium sulfate. The crude oil was chromatographed (CH2Cl2, 1%-5% MeOH/CH2Cl2) to obtain 2-[3-2,2-dimethyl-propionylamino)-pyridin-4-yl]-N,N-diisopropylbenzamide as a white solid. 1H NMR (DMSO-d6, 300 MHz) δ 9.08 (s, 1 H), 8.64 (s, 1 H), 8.43 (d, 1H), 7.58–7.48 (m, 2 H), 7.40 (dd, 1 H), 7.33 (d, 1 H), 7.24 (dd, 1 H), 3.53–3.36 (m, 2 H), 1.38 (d, 3 H), 1.01 (d, 3 H), 0.97 (s, 9 H), 0.91 (d, 3 H), 0.77 (d, 3 H); MS (ES+)=382.

Workup

concentrationwas concentrated in vacuo
extractionextracted with EtOAc
washwashed with brine
dry with materialdried with sodium sulfate
customThe crude oil was chromatographed (CH2Cl2, 1%-5% MeOH/CH2Cl2)

Sources & evidence

ORD record: ord-93f33e1f10f84f3f873fd07cdee15655
Source dataset: uspto-grants-2007_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07235557B2

Reaction notes

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