Sodium Carbonate → HCID 66999892, compound

HRID 558151Notes

Reaction equation

HRID 558151 reaction equation
C(=O)([O-])[O-].[Na+].[Na+].[C:7]([O:11][C:12](=[O:31])[NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1B1OC(C)(C)C(C)(C)O1)([CH3:10])([CH3:9])[CH3:8].Br[C:33]1[C:38]2[S:39][C:40]([C:42]3[C:47]([F:48])=[CH:46][N:45]=[C:44]([NH:49][CH2:50][CH2:51][N:52]4[CH:56]=[CH:55][N:54]=[N:53]4)[N:43]=3)=[CH:41][C:37]=2[CH:36]=[CH:35][CH:34]=1>O1CCOCC1.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]>[C:7]([O:11][C:12](=[O:31])[NH:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:33]1[C:38]2[S:39][C:40]([C:42]3[C:47]([F:48])=[CH:46][N:45]=[C:44]([NH:49][CH2:50][CH2:51][N:52]4[CH:56]=[CH:55][N:54]=[N:53]4)[N:43]=3)=[CH:41][C:37]=2[CH:36]=[CH:35][CH:34]=1)([CH3:8])([CH3:9])[CH3:10]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66738145HCID 66738145, compoundHCID 67000000tert-butyl 2-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)phenethylcarbaMate

Product 1

HCID 66999892HCID 66999892, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

Add a solution of 2 M sodium carbonate (1.08 mL, 2.16 mmol) to a suspension of {2-[2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (0.5 g, 1.08 mmol), [4-(7-bromo-benzo[b]thiophen-2-yl)-5-fluoro-pyrimidin-2-yl]-(2-[1,2,3]triazol-1-yl-ethyl)-amine (450 mg, 1.08 mmol), and Pd(dppf)Cl2 (45 mg, 53.99 μmol) in 1,4-dioxane (4.32 mL) and heat at 100° C. for 4 h. Cool to RT and concentrate. Suspend the residue in DCM and filter through a 2-cm pad of silica in a 60-mL sintered glass funnel Elute with 50 mL DCM and 50 mL (1:1 ethyl acetate/hexane). Then elute with 200 mL of ethyl acetate to collect the product. Concentrate and purify on silica eluting with 10% ethanol in 1:1 DCM/hexane to give the title compound. MS (ES) m/z 560 [M+1]+.

Workup

  1. temperatureCool to RT
  2. concentrationconcentrate
  3. filtrationfilter through a 2-cm pad of silica in a 60-mL sintered glass funnel
  4. washElute with 50 mL DCM and 50 mL (1:1 ethyl acetate/hexane)
  5. washThen elute with 200 mL of ethyl acetate
  6. customto collect the product
  7. concentrationConcentrate
  8. custompurify on silica eluting with 10% ethanol in 1:1 DCM/hexane

Sources & evidence

ORD record
ord-8c843e1166cb43189379bf2be7a6b3f9
Source dataset
uspto-grants-2011_11
Patent number
US08063035B2

Reaction notes

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