Sodium Carbonate → HCID 67313768, compound

HRID 2179633Notes

Reaction equation

HRID 2179633 reaction equation
Br[C:2]1[CH:16]=[CH:15][CH:14]=[CH:13][C:3]=1[CH2:4][NH:5]C(=O)OC(C)(C)C.B1(B2OC(C)(C)C(C)(C)O2)OC(C)(C)C(C)(C)O1.C([O-])(=O)C.[K+].[ClH:40].[N:41]12[CH2:48][CH2:47][CH:44]([CH2:45][CH2:46]1)[C@@H:43]([NH:49][C:50]([C:52]1[S:53][C:54]3[C:60](Br)=[CH:59][CH:58]=[CH:57][C:55]=3[CH:56]=1)=[O:51])[CH2:42]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:40].[ClH:40].[NH2:5][CH2:4][C:3]1[CH:13]=[CH:14][CH:15]=[CH:16][C:2]=1[C:60]1[C:54]2[S:53][C:52]([C:50]([NH:49][C@@H:43]3[CH:44]4[CH2:45][CH2:46][N:41]([CH2:48][CH2:47]4)[CH2:42]3)=[O:51])=[CH:56][C:55]=2[CH:57]=[CH:58][CH:59]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 517044Potassium AcetateHCID 2733548Bis(pinacolato)diboraneHCID 70183002-Bromo-N-(tert-butoxycarbonyl)benzylamineHCID 66904832N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride

Product 1

HCID 67313768HCID 67313768, compound

Reagents, catalysts & solvents 2

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

Procedure

534.2 mg (1.87 mmol) of tert-butyl 2-bromobenzylcarbamate, 474.1 mg (1.87 mmol) of bis(pinacolato)diboron, 397.0 mg (4.04 mmol) of potassium acetate, 45.5 mg (0.06 mmol) of PdCl2(dppf), 500 mg (1.24 mmol) of N-[(3R)-1-azabicyclo[2.2.2]oct-3-yl]-7-bromo-1-benzothiophene-2-carboxamide hydrochloride (Example 8A), 3.11 ml of 2 M sodium carbonate solution and a further 45.5 mg (0.06 mmol) of PdCl2(dppf) in 6.0 ml of DMF are reacted by general method D. Purification by preparative HPLC is followed by concentration of the combined product fractions, taking up in methanol, addition of 1N hydrochloric acid, and stirring at room temperature for 30 min. Concentration and drying under high vacuum result in 121 mg (20% of theory) of the title compound.

Workup

  1. customPurification by preparative HPLC
  2. additionaddition of 1N hydrochloric acid
  3. concentrationConcentration
  4. customdrying under high vacuum

Sources & evidence

ORD record
ord-d39cb98df6464a61a2a60a101c8bd849
Source dataset
uspto-grants-2015_06
Patent number
US09067931B2

Reaction notes

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