Ammonia → HCID 67970318, compound

HRID 1470745Notes

Reaction equation

[CH3:1][CH:2]([NH:16][C:17](=[O:19])[CH3:18])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]2)=[CH:6][CH:5]=1.Br[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH2:28][CH3:29])=[CH:23][CH:22]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Cl.N>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.C(O)(C)(C)C>[CH2:28]([O:27][C:24]1[CH:25]=[CH:26][C:21]([N:13]2[CH2:12][CH2:11][CH:10]([C:7]3[CH:6]=[CH:5][C:4]([CH2:3][CH:2]([NH:16][C:17](=[O:19])[CH3:18])[CH3:1])=[CH:9][CH:8]=3)[CH2:15][CH2:14]2)=[CH:22][CH:23]=1)[CH3:29]

Participants

Conditions

Temperature: 150 °C

Procedure

3.0 mL Toluene/tert-butanol (5:1) are added to a mixture of 130 mg (0.50 mmol) N-[1-methyl-2-(4-piperidin-4-yl-phenyl)-ethyl]-acetamide (VIII.1), 100 mg (0.50 mmol) 1-bromo-4-ethoxy-benzene, 80 mg (0.83 mmol) sodium tert-butyrat, 20 mg (0.040 mmol) X-Phos and 10 mg (0.040 mmol) palladium(II) acetate. The mixture is stirred for 10 min at 150° C. under microwave irradiation in a sealed tube. After that time, the mixture is poured into 1 mL 0.1 N HCl. 1 mL conc. ammonia is added and the mixture is extracted with ethyl acetate (3×). The combined organic layers are dried over sodium sulphate and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel; DCM/MeOH 19:1) to yield the desired product.

Workup

extractionthe mixture is extracted with ethyl acetate (3×)
dry with materialThe combined organic layers are dried over sodium sulphate
customthe solvent is removed in vacuo
customThe residue is purified by column chromatography (silica gel; DCM/MeOH 19:1)

Sources & evidence

ORD record: ord-1301d59892a94b949a42a1eb9f74739f
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006450B2

Reaction notes

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