Sodium Carbonate → HCID 67315355, compound

HRID 2179724Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[ClH:7].[N:8]12[CH2:15][CH2:14][CH:11]([CH2:12][CH2:13]1)[C@@H:10]([NH:16][C:17]([C:19]1[O:20][C:21]3[C:27](Br)=[CH:26][CH:25]=[CH:24][C:22]=3[CH:23]=1)=[O:18])[CH2:9]2.[C:29]([C:32]1[S:36][C:35](B(O)O)=[CH:34][CH:33]=1)(=[O:31])[CH3:30]>CN(C=O)C.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[ClH:7].[C:29]([C:32]1[S:36][C:35]([C:27]2[C:21]3[O:20][C:19]([C:17]([NH:16][C@@H:10]4[CH:11]5[CH2:14][CH2:15][N:8]([CH2:13][CH2:12]5)[CH2:9]4)=[O:18])=[CH:23][C:22]=3[CH:24]=[CH:25][CH:26]=2)=[CH:34][CH:33]=1)(=[O:31])[CH3:30]

Participants

Conditions

Temperature: 70 °C

Procedure

0.58 ml of 2 M aqueous sodium carbonate solution and 15.9 mg (0.02 mmol) of PdCl2(dppf) are added to a mixture of 150 mg (0.39 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzofuran-2-carboxamide hydrochloride (Example 30A) and 66.1 mg (0.39 mmol) of 5-acetyl-2-thienylboronic acid in 2 ml of DMF. The reaction mixture is heated at 70° C. for 18 h and then filtered through kieselguhr and evaporated to dryness. Purification of the crude product by preparative HPLC, subsequent addition of a 1:1 mixture of methanol and 1N hydrochloric acid, concentration and drying under high vacuum result in 83.6 mg (49.9% of theory) of the title compound.

Workup

filtrationfiltered through kieselguhr
customevaporated to dryness
customPurification of the crude product
additionby preparative HPLC, subsequent addition of a 1:1 mixture of methanol and 1N hydrochloric acid, concentration
customdrying under high vacuum

Sources & evidence

ORD record: ord-dbc0e4fa278b49de8b8ad31a95ef68c5
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09067931B2

Reaction notes

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