Sodium Carbonate → HCID 67313476, compound

HRID 2179623Notes

Reaction equation

HRID 2179623 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[ClH:37].[N:38]12[CH2:45][CH2:44][CH:41]([CH2:42][CH2:43]1)[C@@H:40]([NH:46][C:47]([C:49]1[S:50][C:51]3[C:57](Br)=[CH:56][CH:55]=[CH:54][C:52]=3[CH:53]=1)=[O:48])[CH2:39]2.C(=O)([O-])[O-].[Na+].[Na+]>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:37].[N:38]12[CH2:43][CH2:42][CH:41]([CH2:44][CH2:45]1)[C@@H:40]([NH:46][C:47]([C:49]1[S:50][C:51]3[C:57]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)=[CH:56][CH:55]=[CH:54][C:52]=3[CH:53]=1)=[O:48])[CH2:39]2

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 53257294-(2-bromophenyl)morpholineHCID 66904832N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

Product 1

HCID 67313476HCID 67313476, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst2×HCID 6228DimethylformamideSolvent

Procedure

100 mg (0.41 mmol) of 4-(2-bromophenyl)morpholine, 121.0 mg (0.48 mmol) of bis(pinacolato)diboron, 101.3 mg (1.03 mmol) of potassium acetate, 11.6 mg (0.02 mmol) of PdCl2(dppf), 127.6 mg (0.32 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 8A), 0.79 ml of 2 M sodium carbonate solution and a further 11.6 mg (0.02 mmol) of PdCl2(dppf) in 2 ml of DMF are reacted by general method D. Drying under high vacuum results in 38.9 mg (48% of theory) of the title compound.

Workup

  1. customDrying under high vacuum

Sources & evidence

ORD record
ord-29613fc59cba48199b149f16e33d756a
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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