Dimethyl Sulfoxide → HCID 123644455, compound

HRID 1772161Notes

Reaction equation

HRID 1772161 reaction equation
[C:1]([O:5][C:6](=[O:22])[N:7]([CH:9]([C:11](=[O:21])[NH:12][C:13]1[CH:18]=[C:17](Br)[CH:16]=[C:15]([NH2:20])[N:14]=1)[CH3:10])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[B:23]1(B2OCC(C)(C)CO2)[O:28]CC(C)(C)C[O:24]1.CC([O-])=O.[K+].CS(C)=O>C(Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].Cl[Pd]Cl>[NH2:20][C:15]1[CH:16]=[C:17]([B:23]([OH:28])[OH:24])[CH:18]=[C:13]([NH:12][C:11](=[O:21])[CH:9]([N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:22])[CH3:8])[CH3:10])[N:14]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 517044Potassium AcetateHCID 2734316Bis(neopentyl glycolato)diboronHCID 117902383HCID 117902383, compound

Product 1

HCID 123644455HCID 123644455, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)CatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.41 g, 0.6 mmol) is added to a mixture of tert-butyl-N-{1-[(6-amino-4-bromopyridin-2-yl)carbamoyl]ethyl}-N-methyl-carbamate B1 (5.2 g, 11.2 mmol), bis(neopentyl glycolato)diboron (5.1 g, 22.4 mmol), KOAc (3.3 g, 33.6 mmol) and DMSO (20 ml) under argon atmosphere and the mixture is stirred at 80° C. for 5 h. The mixture is diluted with DCM and extracted with a saturated aqueous sodium hydrogencarbonate solution. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 3.2 g (85%). HPLC-MS: M+H=339; tR=0.51 min (Method—2).

Workup

  1. extractionextracted with a saturated aqueous sodium hydrogencarbonate solution
  2. dry with materialThe combined organic layers are dried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe product is purified by RP HPLC

Sources & evidence

ORD record
ord-984811661e6c492d8c8cfbbdccb2527d
Source dataset
uspto-grants-2016_02
Patent number
US09249151B2

Reaction notes

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