Dimethylformamide → HCID 57898988, compound

HRID 911043Notes

Reaction equation

HRID 911043 reaction equation
Br[C:2]1[C:3]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1.[CH2:26](B1C2CCCC1CCC2)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>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.O>[CH2:26]([C:2]1[C:3]([O:15][C:16]2[CH:25]=[CH:24][CH:23]=[C:22]3[C:17]=2[CH:18]=[CH:19][CH:20]=[N:21]3)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH3:14])[N:13]=2)=[N:6][CH:7]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 41509249-Benzyl-9-borabicyclo(3.3.1)nonaneHCID 86634762HCID 86634762, compound

Product 1

HCID 57898988HCID 57898988, compoundYield 9.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A vial was charged with 1,1′-bis(diphenylphosphino)ferrocene-dichloropalladium(II) (0.0199 g, 0.0242 mmol), N-(5-bromo-4-(quinolin-5-yloxy)pyridin-2-yl)-4-methylthiazol-2-amine (0.100 g, 0.242 mmol), 9-benzyl-9-bora-bicyclo[3.3.1]nonane (1.45 ml, 0.726 mmol), cesium carbonate (0.237 g, 0.726 mmol), DMF (5 mL), and water (1.5 mL). The reaction mixture was heated at 80° C. for three days. Water was added and the reaction mixture was extracted with ethyl acetate. The organic layer was dried and concentrated. The crude material was purified by reverse phase column chromatography to give the title compound (0.010 g, 9.25% yield) as a white solid. 1H NMR (CDCl3) δ 8.85 (dd, 1H), 8.17 (s, 1H), 7.96 (d, 1H), 7.60 (t, 1H), 7.56 (d, 1H), 7.25 (m, 3H), 7.22 (s, 1H), 7.19 (m, 1H), 7.15 (dd, 1H), 7.04 (d, 1H), 6.05 (s, 1H), 5.75 (s, 1H), 4.04 (s, 2H), 1-69 (s, 3H).

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe crude material was purified by reverse phase column chromatography

Sources & evidence

ORD record
ord-dd44e408d25d479a9504f44d58a4ad3c
Source dataset
uspto-grants-2011_09
Patent number
US08022222B2

Reaction notes

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